37 Top Things To Do In Chicago, IL

February 11, 2023

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37 Top Things To Do In Chicago, Illinois

I recently took this amazing fall trip to Illinois. If this post inspires you to travel to Illinois, make sure to check ahead for up-to-date events, exhibits and opening hours at any attractions.

Hello from Chicago, Illinois! Chicago is known as the Windy City, not just because of the gusts of frigid air coming off of the lake in winter (and throughout the year), but according to History.com, the city gained its nickname as early as the 1870s as “a metaphorical jab at its supposedly boastful citizenry” and politicians who were “full of wind.”

Chicago has its own distinct culture with its own set of entirely Chicagoan traits – deep dish pizza, smoky jazz bars, Lake Michigan, the Chicago Cubs, and tough Midwesterners.

SEE ALSO: 31 Best Chicago Restaurants in Chicago You Have To Eat At

I went out to Chi-town for three and a half days but could have easily stayed for a month. Below is my travel guide to the Windy City, and while there are many things to do, this really only scratches the surface.


Cloud Gate at Millennium Park in Chicago

Take a picture at Cloud Gate at Millennium Park

Millennium Park is one of the top attractions in Chicago, famed for its stunning array of art and architecture. Perhaps the most iconic feature of Millennium Park is “Cloud Gate,” also known as “The Bean,” which is a giant mirrored orb reflecting the city skyline. Millennium Park is more than just “Cloud Gate” though; it is also home to many other outdoor installations, including Millennium Monument (a nearly full-size replica of a peristyle that originally stood on the corner), Lurie Garden, “Crown Fountain,” and Jay Pritzker Pavilion. Whether you are looking for sweeping city views or quiet garden spaces, Millennium Park offers something for everyone who loves taking photos.

Beyond photo taking, I recommend checking out the bike rentals over at Bike and Roll Chicago to cover more ground and really see the area. If you’re around in the winter months, there’s an ice skating rink perfect for the Christmas season.

201 E Randolph St, Chicago, IL, chicago.gov/city/en/depts/dca/supp_info/millennium_park.html


The Loop

The Chicago Loop, also known as The Loop, is one of the busiest neighborhoods in the city of Chicago, especially on weekdays. This bustling neighborhood is known for its countless skyscrapers, busy business district, and vibrant culture. The Loop is home to some of Chicago’s most famous attractions, including Millennium Park and The Art Institute of Chicago. Whether you’re a tourist exploring the area and viewing the sights from high atop a skyscraper, or a local looking for some great shopping along North Michigan Avenue and after-work dining options, The Loop has something for everyone. So, if you’re ready to dig into the quintessential urban experience in the Windy City, this is the place to be as it truly epitomizes everything that makes Chicago great.


360 CHICAGO Observation Deck

There’s no better place to take in all the amazing views of the city than 360 CHICAGO. This popular attraction, located on the 94th floor of the former John Hancock Center, is a must-see for any visitor or local looking to experience some of Chicago’s best sights and attractions from a different perspective. Sunset is the best time to visit, as you can really soak up the stunning city views, but after dark is fun too when the city is all lit up below you.

Inside 360 CHICAGO you’ll find all kinds of fun things to do and see, from relaxing while you enjoy a drink with friends at CloudBar at 360 Chicago to experiencing TILT – Chicago’s highest thrill ride. Finish your visit at The Signature Lounge for cocktails on the 96th floor of this famous skyscraper.

Ticket cost:

  • Admission tickets only to get views from the 94th- Adult (12 year old +) from $30; Youth from $20
  • Tilt and View-Adult (12 year old +) from $39; Youth from $29
  • Sip, TILT, and View- Adult (12-year-old +) from $49; Youth from $34

875 N Michigan Ave, Chicago, IL, 360chicago.com


Skydeck Chicago

Skydeck Chicago is another popular space to take in stunning views of the city skyline. Skydeck is located on the 103rd floor of the Willis Tower. Visitors can step out onto The Ledge, a glass-enclosed space that allows them to look straight down to the streets below. Skydeck Chicago is a great choice for anyone looking for an exhilarating experience and an alternate option to 360 Chicago.

233 S Wacker Dr, Chicago, IL, theskydeck.com


Shoreline Architecture River Tour in Chicago Illinois

Shoreline Architecture River Tour

Taking the Shoreline Architecture River Tour in Chicago is an absolute must for anyone interested in Chicago architecture or travel enthusiasts interested in the skyscrapers that dot downtown Chicago. Whether you choose to start your tour from the dock at Lake Michigan over at Navy Pier or start in the middle of the Chicago River just off the Magnificent Mile on Michigan Avenue, you will experience some of the most impressive buildings and structures that make Chicago the architectural gem that it is today.

On this educational architecture tour, you will be treated to captivating stories and fascinating insights about the design and engineering behind some of the city’s most famous landmarks. From world-renowned monuments, like Millennium Park and the Willis Tower, to lesser-known gems such as Goose Island, you will feel like you know Chicago better than the locals after this river cruise.

Ticket cost:

  • Adults: $43 – $47
  • Children (3-12): $24 – $28
  • Children 2 and under: Free

401 N Michigan Ave, Chicago, IL, shorelinesightseeing.com


Explore shops on State Street

Chicago’s State Street is a shopper’s paradise with everything from high-end department stores to bargain options all within walking distance of each other. If you’re looking for a central location to do some serious damage during your shopping spree, this is the place to be. Here are some of the best places to hit up during your time on State Street.

  • Macy’s on State Street is a historic department store (formerly the Marshall Field and Company Building) that has been serving Chicago shoppers since 1852 when it was owned by P. Palmer & Co. In recent years, Macy’s has undergone a multi-million dollar renovation to modernize the store and create a more luxurious shopping experience. Macy’s is the place to go if you’re looking for designer labels and high-end fashion in the heart of the city.
  • Block 37 is a modern shopping mall filled with retail stores and restaurants. This is the perfect spot if you’re looking for mainstream brands like H&M, Forever 21 and Best Buy. Block 37 also has a movie theater, a climbing gym and indoor golf simulators.
  • Merz Apothecary is an iconic Chicago institution that has been serving customers since 1875. This old-fashioned apothecary specializes in natural health remedies and beauty products. Merz Apothecary is worth checking out if you’re looking for unique gifts or hard-to-find items.
  • Nordstrom Rack is the off-price sister store of Nordstrom, so you can expect to find designer brands at deeply discounted prices. Shoppers love Nordstrom Rack for its wide selection of shoes, handbags, and clothing for men, women and children. This is a great place to start your State Street shopping spree if you’re on a budget, but still love the finer things in life.

State Street in Chicago is a shopper’s paradise with something for everyone regardless of their budget. No shopping trip is complete for me without a stop at Sephora and UNIQLO, which can both be found on State Street. As you can see, from high-end department stores to trendy fast fashion retailers, you’ll find it all here.


Explore Navy Pier

Navy Pier is one of Chicago’s most popular tourist destinations, and it’s easy to see why. With its diverse array of attractions, there’s something for everyone at Navy Pier. Whether you’re looking for a unique experience such as kayaking on Lake Michigan, taking in the skyline from the Centennial Wheel (a Ferris wheel), or simply going for a stroll, Navy Pier’s got it all!


Ride the Centennial Wheel (Ferris Wheel)

One of the first things you’ll notice when you arrive at Navy Pier is the Centennial Wheel a large Ferris wheel. Standing at 150 feet tall, the Ferris wheel is hard to miss. Taking a ride on the Ferris wheel is a must-do when you’re at Navy Pier. From up high, you’ll get breathtaking views of Lake Michigan, the city skyline, and beyond.


Offshore Rooftop Bar

The Offshore Rooftop bar in Chicago is a sleek, modern rooftop bar that offers stunning views of Lake Michigan and the Chicago skyline. This venue is perfect for chef-driven Californian cuisine and craft cocktails and provides a unique experience that cannot be found anywhere else. With its large rooftop deck, cozy fire pits, and sweeping lake views, Offshore Rooftop is the perfect place to relax and enjoy the beauty of Chicago.

1000 E Grand Ave, Chicago, IL, offshorerooftop.com


Breakfast at Beatrix

Beatrix is the perfect healthy breakfast spot for busy Chicagoans or those trying to get energized for a day of wandering. This neighborhood coffeehouse also functions as a full-service restaurant serving not only breakfast and brunch but lunch and dinner as well. The extensive coffee menu offers a variety of caffeinated drinks using their own house blends from Beatrix Coffee Roasters. Those looking for a healthy breakfast option can enjoy ten-grain oatmeal or Greek yogurt and berries, while egg aficionados will love the omelets.

If you aren’t counting calories and you are looking for something a bit more adventurous, Beatrix offers Mexican breakfast tacos and North African/Middle Eastern shakshuka. There are also pancakes with housemade lemony syrup for those with a sweeter tooth. And finally, the pastries are fresh and come in both gluten-free and regular options. Beatrix has several locations, including Fulton Market, The Loop, River North and Streeterville neighborhoods, plus the suburb of Oak Brook.

671 N St Clair St, Chicago, IL, beatrixrestaurants.com


Ramen-San ramen restaurant in Chicago Illinois

Dinner at Ramen-San

Ramen-San is a popular neighborhood ramen joint where noodles and hip-hop meet. I recommend starting with the Spicy Szechuan Chicken wings to warm you up, followed by the crowd-favorite Tonkotsu Ramen. Note that you can add some sides, such as kimchi or buttered corn, to your noodles. If you’re hungry, try the Sumo Bowl, a hearty meal with tons of meat. Beyond their original location in River North, there’s also Ramen-San Whisky Bar in Fulton Market, which has a large collection of Japanese whiskeys, and over in Streeterville, Ramen-San Deluxe, which extends its menu with sushi options.

59 W Hubbard St #2, Chicago, IL, ramensan.com


Cocktails at ZBar

Located at The Peninsula, Z Bar is the perfect place to go for a date night or some nightlife with friends. The bar has a new menu that could be described as exotic and bold, featuring worldly flavors, and the cuisine provides elevated international shareable bites and satisfying small plates. The small plates that jumped out to me include- tuna tartare, burrata, caviar potato bites and West Coast oysters. Try the adobo glazed chicken wings or seasonal sliders if you’re sharing. The bar also has a great selection of beverages, including rare spirits used innovatively and small-batch bitters that can’t be found anywhere else. The cocktail menu had four sections- ‘Tried and True’, ‘Something New’, ‘The Finer Things’ and ‘G+T’. The ‘Finer Things’ included $60 drinks named Scotch + Champagne, Mad Sound, and Mademoiselle. Wanting to mix it up, we tried out these cocktails: “Z”, “Bangkok Jam” and “Surprise, Surprise.” All are distinctly unique in flavor and worth the trip back for a second.

108 E Superior St, Chicago, IL 60611


Aviary bar in Chicago IL


The Aviary is a unique cocktail experience brought to you by the Alinea Group, popular with Chicagoans and those from out of town. Here they have perfected state-of-the-art beverages that promise to be unlike anything else. The prix fixe menu includes 3 cocktails for $65 and $25 more for food pairings. The night starts off with a complimentary warm cocktail to prepare you for the adventure ahead.

For the first course, I had the “Let The Games Be-Gin” – a savory gin and tonic that ended up being my favorite of all the cocktails. For the second course, “Peach Better Have My Honey” was a warmed toddy with a bunsen burner demonstration. For my third course, I picked both the “Tropic-like It’s Hot,” which reminded me of mulled wine (pictured above), and “(719)26-OATES,” a boozy cocktail served inside an ice ball that you break open. Truly an ultimate, elevated cocktail experience that you cannot miss in Chicago.

Reservations in advance are highly advised given Aviary’s popularity!

955 W Fulton Market, Chicago, IL, theaviary.com


kumiko bar in chicago IL

Cocktails at Kumiko

At Kumiko, an upscale Japanese dining bar in Chicago’s West Loop, owner and mixologist Julia Momosé draws on Japanese ingredients and techniques to create a menu of innovative drinks and dishes that are truly outstanding. Whether you are stopping by for some one-of-a-kind saké or coming with friends for a romantic meal, Kumiko treats all guests to warmth and gratitude.

With its creative Japanese fare and expertly crafted cocktails, including an omakase tasting menu composed of Kumiko’s best drinks and dishes, Kumiko is a must-visit destination for those who are serious about food and drinks. The bar boasts an extensive list of sake, rice whiskey, Japanese whiskey, and shochu. Further, their signature drinks include the Hanamizake Martini, Moonrise Daiquiri, and the Bermutto Sazerac. The modern ambiance, elegant decor, and dim lighting all contribute to the restaurant’s luxurious vibe, making it one of the best bars in the world according to Worlds50bestbars.com. So if you’re looking for an exciting night out on the town, be sure to leave the kids at home – Kumiko is strictly 18+.

630 W Lake St, Chicago, IL, barkumiko.com


Chinatown Food & Culture Walking Tour with Bobby’s Bike Hike Chicago

Chinatown Food & Culture Walking Tour with Bobby’s Bike Hike Chicago

This food and cultural walking tour with Bobby’s Bike Hike Chicago is a great way to learn about Chinese immigration to Chicago while indulging in some delicious food. You’ll sample delicacies from five different regions of China, and can expect to try things like Szechuan chicken, hot pot, dim sum, tea and baked goods. The guides on this food tour are very knowledgeable and passionate about the history of Chinatown, and they will share lots of interesting stories and facts with you. Beyond my own personal recommendation as a foodie, Bobby’s Bike Hike Chicago tour was awarded TripAdvisor’s Travelers’ Choice Best of the Best 2022 in Chicago Tours.

Prices vary depending on the day of your tour, but adult tickets usually cost around $55. Tours get packed and start at 4 p.m. on Friday and Saturday, so be sure to book in advance. Bobby’s Bike Hike Chicago also offers other great tours, like a dessert walking tour plus several foods and cultural bike tours.

Stops on our tour:

  • Phoenix Restaurant
  • Lao Sze Chuan
  • Shan Shaan Taste 山陕名吃 (Xi’an Cuisine 西安菜)
  • Elite Tea
  • Chiu Quon Bakery & Dim Sum
  • Yummy Yummy Noodles

Hyde Park

Hyde Park, on Chicago’s southside, is one of the city’s most popular tourist destinations, known for its leafy green spaces and vibrant cultural scene. Visitors can enjoy strolling through the historic sites or soaking up the sun at a local park

The area was originally developed as farmland in the mid-1800s, and many of the original farmhouses can still be seen today. Over time, however, Hyde Park became a cultural center and home to the University of Chicago, housing numerous art galleries and theaters alongside beautiful public spaces, like the Smart Museum of Art, as well as Frank Lloyd Wright’s Frederick C. Robie House. There are also plenty of opportunities to catch live music or enjoy a delicious meal at one of Hyde Park’s many trendy restaurants and cafes, including two Michelin Bib Gourmand restaurants – Nella Pizza e Pasta and Virtue.

Lincoln Park

Lincoln Park and the Lincoln Park Zoo

Lincoln Park is a neighborhood located on the North Side of Chicago, and one of the most affluent neighborhoods in Chicago. It is also home to Lincoln Park, one of the largest parks in the city. The park is known for its lush landscaping, views of Lake Michigan, and attractions like the Lincoln Park Conservatory.

Many visitors (especially families) come to the park for the Lincoln Park Zoo, one of the country’s oldest free zoos. Other notable attractions in Lincoln Park include the Peggy Notebaert Nature Museum, Chicago History Museum and Theater on the Lake.

2001 N Clark St, Chicago, IL, lpzoo.org


Explore the Lakefront

Get your heart racing at the Lakefront Trail, an 18-mile path along the shore of Lake Michigan. The trail is perfect for activities like biking, running and walking. There are also a number of beaches along the trail where visitors can take a dip in the lake. The Lakefront Trail is a great way to see some of Chicago’s most beautiful scenery while you sneak in a little exercise on your trip..

Lakefront Trail, Chicago, IL, chicagoparkdistrict.com/parks/lakefront-trail/


Shopping on W Armitage Ave

If you’re looking for a hip and trendy area to explore in Chicago, head over to Lincoln Park and check out Armitage Avenue and Halsted Street. These two streets are home to some of the coolest independent shops in the city, including Green Goddess Boutique and Second Time Around.

J9 Wine Bar is a great spot to stop for a drink, featuring an extensive wine list and cocktail menu. If you’re in the mood for French cuisine, Chez Moi is the perfect place to go. They offer a casual atmosphere and a wide variety of wines.

Our favorite shops in the area included:

  • Art Effect: If you’re looking for something unique to buy, be sure to check out Art Effect. They have some amazing jewelry, clothes and home decor items for sale.
  • Bedside Manor Ltd is perfect for anyone in the market for something new for their home.
  • All Birds is a sustainability advocate selling eco-friendly products
  • Outdoor Voices provides the perfect atmosphere while you shop their large selection of activewear.
  • Topdrawer has beautiful leather goods.
  • Mugsy is your home for menswear and the perfect pair of jeans.
  • Bliss & Belle is for the ladies in need of cute clothing and accessories with a splash of unique gifts.

Numerous other shops dot West Armitage Ave, making this a great alternative to the more popular shopping scenes in the city.


Oz Park - The Wizard of Oz Statues in Chicago Illinois

Oz Park – The Wizard of Oz Statues

Oz Park is a beautiful green oasis nestled in the heart of Chicago’s bustling Lincoln Park neighborhood. Located between Oz Street and Emerald Street, this little gem of a park is a dream come true for fans of “The Wizard of Oz!” While the park is the perfect spot to relax and unwind in nature, featuring charming landscaping, lush grassy meadows, and lovely walking paths, it’s the statues of the beloved characters from the classic book by L. Frank Baum that most people usually come to see.

In the early 1990s, the Oz Park Advisory Council and the Lincoln Park Chamber of Commerce hired sculptor John Kearney to create a statue of the Tin Man. The Cowardly Lion, Scarecrow and Dorothy & Toto would join the Tin Man, making the quintet complete by 2007. Other Oz features include the “Emerald Garden” and “Dorothy’s Playlot,” a favorite spot for parents and children. Oz Park is truly a must-see for any fan of “The Wizard of Oz” as this magical park truly captures all the wonder and charm of Oz itself.

2021 N Burling St, Chicago, IL 60614


Dash of Salt & Pepper in Chicago, Illinois

Breakfast at Dash of Salt & Pepper

Dash of Salt & Pepper is a beloved diner in Chicago’s Lincoln Park neighborhood that serves up classic American comfort foods from an open kitchen line. Whether you’re chasing a cup of coffee in the morning or craving something sweet for lunch, this funky spot is the perfect place to satisfy your need to fuel up for the day.

Popular dishes offered for breakfast at Dash include Pop-Tarts, Jorge’s Breakfast Quesadilla, Irish Breakfast and Chilaquiles. Beyond these delicious options, they also have a wide range of classic breakfast items that will please any crowd. If you are really hungry, order one of their breakfast sandwiches, available with your choice of fresh fruit, crispy hash browns or creamy grits on the side. It’s easy to see why breakfast at Dash remains one of the most popular spots in Lincoln Park.

2201 N Lincoln Ave, Chicago, IL, dashsnp.com


Chicago Style Hot Dog at The Wiener's Circle in Chicago

Chicago Style Hot Dog at The Wiener’s Circle

The Weiners Circle is one of the most iconic spots in Chicago, known for its delicious Chicago-style hot dogs and world-famous footlong chili fries. The restaurant has been a classic Midwest institution in the city for decades, drawing lines of hungry patrons all day long.

The bustling atmosphere and cranky staff are a big part of The Weiners Circle’s charm, but the food really sets it apart. The signature Chicago-style hot dog is different from other hot dog variations in that it features relish, onions, green peppers, pickles, a dill pickle spear, tomato slices or wedges, hot peppers, and celery salt – all on a soft poppy seed bun. Beyond their Chicago-style dogs, the famously surly staffers serve char dogs and more at this tiny institution that’s open late. The result is a hearty and unique meal that truly captures the spirit of this vibrant city.

Whether you’re visiting The Weiners Circle for the first time or are a longtime fan of its famous fare, I guarantee that you won’t be disappointed by this one-of-a-kind culinary experience!

​​2622 N Clark St, Chicago, IL 60614


Pequod’s Pizza in Chicago

Pequod’s Pizza

Pequod’s Pizza is a legendary Chicago institution renowned for its famous deep-dish pizza with a caramelized crust. This style of pizza is unlike anything you will find elsewhere – the thick crust is intensely flavorful and topped with layer upon layer of gooey cheese and savory sauce. Since its opening in the 1970s, Pequod’s has been serving up some of the best pizza in the state, drawing crowds of hungry Chicagoans and tourists willing to make the short trek to the original spot over at Morton Grove. They’ve also got a more convenient location in Lincoln Park. Visit either location and see why Pequod’s is the gold standard for deep-dish pizza lovers!

2207 N Clybourn Ave, Chicago, IL, pequodspizza.com


Wrigley Field Tour in Chicago Illinois

Wrigley Field Tour and Photo Op at Wrigley Field Sign

A tour of historic Wrigley Field is a must-do for baseball fans and enthusiasts. The ballpark has been around for more than 100 years and is home to the Chicago Cubs (major league baseball team). The 90-minute tour provides visitors with a look at the beauty and charm of Wrigley Field, as well as some of its historic features. Depending on whether it is a game day or not, the tour may vary, but typically includes access to the seating bowl, press box, Budweiser Bleachers, outfield ivy, visiting team’s clubhouse, Cubs’ dugout and the field. Fans will also have the opportunity to have their photo taken at the iconic Wrigley Field sign. Tip: The photo can be done outside of the stadium even if you don’t do the tour.

Ticket cost: Individuals: $30 (plus tax), Children under two years old are free

1060 W Addison St, Chicago, IL, mlb.com/cubs/ballpark/tours

Goose Island

Jack’s Pumpkin Pop-up in Chicago Illinois

Jack’s Pumpkin Pop-up

Spanning two acres, Jack’s Pumpkin Pop-Up is a seasonal event on Goose Island. Back in its fifth year, I was stoked to be able to attend this festive event. They’ll be back next September, but I know many of you follow me to hear about where to get seasonal artisanal beers and specialty cocktails, and this five-week event (September 22-October 31, 2022, dates for 2023 to be announced) didn’t disappoint. The field was stocked with more than 10,000 pumpkins, the city’s largest corn maze, and a hidden bar. Jack’s Pumpkin Pop-up is family-friendly, and those with kids will love the photo ops in front of numerous backdrops. Adults looking for a more lively scene will get that after 7 pm when the space becomes an adult-only venue (think four full-service bars, ax throwing and classic carnival games).

1265 W Le Moyne St, Chicago, IL, jackspumpkinpopup.com

Wicker Park

Wicker Park in Chicago Illinois

Explore Wicker Park

Located just northwest of downtown Chicago, the hipster neighborhood of Wicker Park is a great area to pass your time in the Windy City. Filled with cool bars, trendy restaurants and independent shops, Wicker Park has something for everyone, including its small-town feel. The neighborhood is anchored by the park after which it’s named—a 16-acre green space that’s perfect for a leisurely stroll or picnic on a nice day.

First-time visitors will find plenty of places to eat, drink and shop in Wicker Park too. For breakfast or brunch, head to Publican Quality Bread. This local bakery specializes in wood-fired pizzas and sandwiches made with freshly baked bread. For dinner, check out Big Star—a taco joint frequented by locals. Be sure to order one of their delicious margaritas to wash down your meal.

No trip to Wicker Park would be complete without spending some time exploring the neighborhood’s many bars. If you’re looking for a laid-back spot to grab a drink, The Revel Room has great cocktails in a bar filled with vintage furniture and books lined up on a wall in a library-like fashion. If you’re hoping to catch some live music, head over to The Empty Bottle instead. This dive bar hosts local and touring bands almost every night of the week.

Wicker Park is one of the premier vintage shopping destinations in Chicago, and on Milwaukee Avenue especially, you’ll find a wide variety of great shops. Some of the highlights include Reckless Records, with its huge selection of vinyl records and music paraphernalia and Myopic Books for rare used books and literary collectibles. Pop into Ipsento Coffee for a delicious cup of coffee or a quick bite to eat to keep you caffeinated as you continue to explore.

Besides these unmissable shopping spots, there were plenty of other interesting places to explore in Wicker Park that I would have loved to wander. The streets are dotted with cute cafes and quirky boutiques, while numerous art galleries and performance spaces add a unique cultural vibe to the area.


The 606

Chicago is a city full of surprises, and one of the most pleasant surprises is The 606. This 2.7-mile elevated park and trail were built on an abandoned railway line on the city’s northwest side. Today, the popular trail features a chain of street-level parks, scenic look-out points, an observatory, and public art installations.

The 606 is open daily from 6 am to 11 pm, and admission is free. The trail takes you through the trendy neighborhoods of Wicker Park, Bucktown, Logan Square and Humboldt Park. The best way to access the park is via one of the four entry points: Ashland Avenue, Ridgeway Avenue, Walsh Park or Marshall Boulevard.

Once you’re in, you can take your pick of activities. If you’re feeling active, go for a run or walk on the trail. Or take a leisurely stroll and enjoy the views of the cityscape and nature. There are also plenty of benches along the way if you need a break.

In addition to the beautiful scenery, one of the best things about the 606 is all of the public art on display. As you walk or run along the trail, you’ll notice murals, mosaics and sculptures. There’s also an outdoor amphitheater where you can catch live performances in the summer.


Tortello - Italian restaurant in Chicago Illinois

Dinner at Tortello

While I had heard about the many fabulous restaurants in the Wicker Park area, Tortello was one that continued to come up. If you’re looking for a truly authentic Italian dining experience, then look no further than Tortello. This chef-driven restaurant is known for its simple yet delicious dishes, all made from the highest quality ingredients with a focus on traditional Italian cooking. Whether it’s their award-winning red wine, the orange fennel salad that has left a lasting impression, or the mouthwatering homemade pasta, every dish here will surely delight your taste buds. So if you’re looking for an affordable Michelin meal that provides an exquisite culinary experience, be sure to check out Tortello when in the Windy City!

1746 W Division St, Chicago, IL, tortellopasta.com

More things to do in Chicago

The Windy City is filled with tons of things to do, and there was no way I could get through all of it, but I will definitely be returning to further this travel guide. Listed below are some other popular destinations.


Garfield Park Conservatory

Garfield Park Conservatory is one of the largest and most beautiful greenhouses in the city of Chicago. With loads of lush, green pathways to explore and countless species of flowers, trees and plants to discover, it’s no wonder that this iconic conservatory is a favorite among travelers and locals. Whether you’re a keen horticulturist or just someone who enjoys spending time in nature, Garfield Park Conservatory should not be missed.

Stroll through its peaceful gardens on a sunny afternoon or visit during the colder months when everything is blanketed in snow; the conservatory is the perfect spot to warm up when Chicago turns into a winter wonderland. No matter the time of the year, if you’re looking for a transformative experience that will refresh your mind and revitalize your senses, be sure to add Garfield Park Conservatory to your list of must-see attractions in Chicago.

300 N Central Park Ave, Chicago, IL, garfieldconservatory.org/


Grant Park

Situated in downtown Chicago, Grant Park is a public park that attracts visitors from all over. The park offers a wide range of activities and attractions, including gardens, playgrounds, sports facilities, a lakefront trail and more. There are also plenty of restaurants and cafes in the area and cultural attractions just south of the park, including the Field Museum and the Adler Planetarium.

337 E Randolph St, Chicago, IL, chicagoparkdistrict.com/parks/grant-park/


Maggie Daley Park

Maggie Daley Park is home to gardens, a climbing wall, mini golf, a field house and picnic groves. It also has a rollerblading/scooter track that turns into an amazing ice skating rink in winter. The park was named after former First Lady Maggie Daley, whose husband was Richard M. Daley, the former Mayor of Chicago. The park is also a jump-off point for the popular Millennium Park and is a great way to explore Chicago’s shoreline.

337 E Randolph St, Chicago, IL, maggiedaleypark.com


Chicago Riverwalk

The Chicago Riverwalk is a 1.25-mile pedestrian path along the Chicago River, one of Chicago’s most iconic waterways, featuring a variety of shops, restaurants and cafes. The Riverwalk is also home to several boat tours that offer visitors a unique perspective of the city.

Chicago Riverwalk, Chicago, IL, chicagoriverwalk.us/


Chicago Cultural Center

The gorgeous Chicago Cultural Center is a hub for tons of events open to the public, and each year hosts hundreds of free exhibitions, performances and films. The center is also home to two theaters, a state-of-the-art public library, and two gorgeous stained-glass domes, including the largest Tiffany glass dome in the world. For $10 and an appointment, you can also make this your wedding venue!

77 E Randolph St, Chicago, IL, cityofchicago.org


Chicago Theatre

The Chicago Theatre is one of the most iconic landmarks in the city of Chicago. The theater first opened its doors in 1921 and has since been a popular venue for concerts and stage shows. The theater’s architecture is a sight to behold, and the interior is just as impressive. For tourists looking for a taste of the arts, the Chicago Theatre is a must-see.

175 N State St, Chicago, IL, thechicagotheatre.com


Museum Campus

The Museum Campus is home to three world-class museums located in Chicago’s South Loop. You’ll find the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium in this 57-acre campus on the southside of Grant Park. As you can imagine, the campus is a popular tourist destination with more than four million visitors each year. The campus features a walking path and gardens, hosts concerts and festivals throughout the year, and offers a variety of exhibits, programs and educational opportunities for students and guests.

337 E Randolph St, Chicago, IL, chicagoparkdistrict.com/parks-facilities/grant-park/


Museum of Contemporary Art

The Museum of Contemporary Art is a world-renowned institution that attracts tourists from all over the globe. The museum features a variety of exhibitions, ranging from traditional art forms to cutting-edge contemporary pieces. There’s also a cafe and a gift shop on site.

220 E Chicago Ave, Chicago, IL, mcachicago.org


The Field Museum of Natural History

The Field Museum is one of the largest natural history museums in the world. It features a variety of exhibitions on topics like anthropology, meteorites, paleontology, gems and ancient cultures. The museum also has a planetarium, a butterfly conservatory, and you’ll get a chance to see one of the most extensive and intact (to date) Tyrannosaurus rex skeletons named SUE. For those interested in archaeology, natural history, large mammals and dinosaurs, the Field Museum is the ideal place to spend a day.

1400 S Lake Shore Dr, Chicago, IL, fieldmuseum.org


Adler Planetarium

The Adler Planetarium is one of the most popular tourist attractions in Chicago. The planetarium features exhibits on astronomy and space science, as well as a theater where visitors can watch documentaries about the cosmos. The Adler Planetarium is great for tourists to learn more about our solar system and the universe beyond.

1300 S Lake Shore Dr, Chicago, IL, adlerplanetarium.org/


Shedd Aquarium

The Shedd Aquarium is a classic tourist destination that hosts more than 1.5 million visitors annually. The aquarium features exhibits of aquatic life from around the world, including dolphins, sharks and whales. There’s also a large IMAX theater on site showing documentaries about the creatures below the surface. The aquarium is the perfect place for visitors of all ages to learn about the world’s oceans and the creatures that inhabit over 70 percent of our world.

1200 S Lake Shore Dr, Chicago, IL, sheddaquarium.org/


The Art Institute of Chicago

The Art Institute of Chicago is one of the most popular art museums in the world, and it is a must-see for art lovers visiting Chicago. The museum features art from ancient times to the present from around the globe. Guests are welcome to participate in a variety of educational programs and events throughout the year.

111 S Michigan Ave, Chicago, IL, artic.edu


Museum of Science and Industry

The Museum of Science and Industry is one of the largest science museums in the world, featuring a variety of exhibitions covering science, technology, transportation, history and so much more. It is home to the U-505, the only German submarine in the United States, as well as the Giant Dome Theater, Chicago’s only five-story domed movie theater. Guests love watching the 70-foot tornado whirl around its exhibit, interacting with the Pioneer Zephyr exhibit, and of course, the Baby Chick Hatchery, where visitors can watch life begin in the most adorable way.

5700 S Lake Shore Dr, Chicago, IL, msichicago.org


Chicago History Museum

The Chicago History Museum is one of the coolest museums in the city, and it’s all about…you guessed it…Chicago history! The museum features a variety of exhibitions on topics like the Great Chicago Fire, Abraham Lincoln, the mob and gangsters of the past, and the Civil War. The Chicago History Museum is an excellent choice for locals and tourists interested in learning more about the city’s history.

1601 N Clark St, Chicago, IL, chicagohistory.org


Jane Ko is the Austin blogger behind A Taste of Koko, Austin's top food and travel blog featuring the hottest restaurants and weekend getaways. Jane has been a speaker at South by Southwest (SXSW), Texas Conference for Women, BlogHer, and more on entrepreneurship and social media. She lives in Austin Texas with her dog and cat.