The Ultimate Chicago Bucket List
an article by The Apartment Guide
by Holly Hooper
March 18, 2024
Whether you’re into sampling local food or visiting beautiful lakeside beaches, Chicago has something for you to do.
We interviewed local experts to see how they suggest spending a day in the Windy City.
Keep reading to see what you should do with a day in Chicago, depending on your interests.
If you’re contemplating renting an apartment in Chicago, brace yourself for an extraordinary urban journey. Chicago beckons with so much culture, diversity, and excitement, offering a myriad of attractions and iconic landmarks just steps away.
To guarantee you seize every moment in this vibrant cityscape, this ApartmentGuide article presents the quintessential Chicago bucket list, brimming with must-visit destinations and unforgettable adventures.
1. Tour Chinatown
Touring Chinatown in Chicago offers a vibrant cultural experience, from exploring authentic Chinese cuisine to browsing markets filled with unique goods. Visitors can experience the rich history and traditions of this dynamic neighborhood, highlighted by colorful pagodas and ornate architecture.
“Chinatown is a 110+-year-old community that is steps away from downtown where you can experience one of the most unique and authentic neighborhoods in Chicago,” suggests Z.J. Tong, President of Chicago Chinese Cultural Institute, an institute dedicated to cross-cultural understanding by offering training, hospitality, and more for corporations and brings Chinese language and culture programs to schools, libraries and the general public.
“The hottest dining addition to the community at the moment is hot pot restaurants. Stop by Shoo Loong Kan Hotpot for the best restaurant photo op and delicious food. Or Liuyishou Hotpot for its most authentic flavors true to its origin in China.
If you are a fan of Cantonese dim sum, check out Ming Hin at Chinatown Square or Triple Crown in the old town area. Chiu Quon Bakery is another must-stop on old Chinatown’s Wentworth Ave to try the tasty pastry that served Chinatown for generations.
How can you leave Chinatown without a cup of sweet bubble tea? Check out Joy Yee, it’s where the bubble tea tradition started in Chicago, or Teamo, try some of the more sophisticated bubble tea options today. For shaved ice cream, check out the Legend Tasty House on Wentworth Ave in the old Chinatown area.
For history lovers, check out the Chinese American Museum for its exhibits on the community’s rich history. While checking out the wonderful food, make sure you stop by our attractions such as Nine Dragon Wall, Chinatown Gate, Pui Tak Center (historical On-Leong Merchants Association Building), the Zodiac Square and the beautiful Ping Tom Memorial Park. Throughout the summer, the Chicago Chinese Cultural Institute will offer Chinatown tours.”
2. Explore the city on a bike
Explore Chicago's vibrant neighborhoods and iconic landmarks by biking along its scenic lakefront trails, bustling city streets, and charming green spaces, offering a unique and exhilarating way to experience the Windy City's diverse culture and stunning scenery.
Julie Sherman, Ride Chair of the Chicago Cycling Club, a friendly, diverse group of people who share their love of biking. All ages, backgrounds, and level of athletic ability are welcome to join in on rides. Julie shares, “My favorite weekend activity is doing a fun bike ride with the Chicago Cycling Club on one of their fun, informative neighborhood adventure rides to explore all the different parts and secrets of Chicago including some of the suburbs. The rides are at a casual pace so we really get to see, hear, and sometimes smell the different neighborhoods we bike through. We go all over the world on these rides and it often includes a stop somewhere to connect with the other riders over lunch.”
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3. Grab brunch
Indulge in a delightful brunch experience at one of Chicago's charming eateries, then treat yourself to a delectable drink at one of the city's renowned bars, offering an array of tempting options to savor amidst its lively atmosphere.
“I love to start the day off by eating brunch at the Hampton Social in River North,” recommends
Victoria Marinucci, a social media content creator at Nucci Socials, a boutique content creation agency, specializing in storytelling, such as photography, videography, and user-generated content. “It's so cute and a great place to take photos with your friends. After brunch, take a stroll along the Chicago River. To end the day, catch a sunset and grab a cocktail at London House Chicago, then head to Blind Barber for a nightcap.”
4. Bird watching
“One of my favorite things to do is grab a pair of binoculars and ride my bike to the Montrose Point Bird Sanctuary,” says Lesley Tweedie, from Roscoe Village Bikes, a Chicago bike shop that sells bicycles and accessories for kids, recreational riders, urban commuters, and competitive cyclists. “The waterfront and skyline views are beautiful and there are always interesting birds to see. On one visit we saw two owls in the middle of the day. It's a world-class bird-watching spot right in the middle of the city.”
Montrose is truly an idyllic setting for birdwatchers. This is a great place to immerse yourself in the natural surroundings and observe a diverse range of bird species in Chicago.”
5. Get active with some friends
Whether you're a fitness enthusiast or just looking for a fun way to stay active, Chicago's diverse fitness community has something for everyone to enjoy. Local wedding photographer, Gretchen of Gretchen Wittry Photography, suggests, “A perfect Chicago day for me starts at Rise Nation for an energetic, community-centric HIIT workout, followed by a long walk along the lakefront trail with a coffee in hand. Then I'll swing by my favorite market, Foxtrot, to work for a few hours and pick up snacks and drinks before meeting up with friends on their city-view rooftop for the night.”
6. Shop for antiques and books
Enjoy leisurely antique shopping as you stroll through the charming streets of Chicago, discovering unique treasures and hidden gems. Explore quaint bookstores at your own pace, immersing yourself in a world of literary wonders, for a delightful day of leisure and book hunting in the Windy City.
Local photographer, Aline of Aline Stern Photography, shares, “My favorite thing to do on a Sunday morning is meeting friends for brunch at Lost Larson in Andersonville. Afterward, we stroll through Andersonville and check out antiques and second-hand clothes at Brown Elephant and the book recommendations at Women and Children First bookshop.
I also enjoy strolling the residential streets around Clark. I often stop at the Pride House on the block of 1700 W Balmoral, to see which creative new decoration they’ve put up. Their unique displays like the rainbow unicorn support the Trevor Project – an organization that provides aid for the LGBTQ+ community.”
7. Visit Chicago’s diverse restaurants and beaches
Chicago boasts a plethora of restaurants offering diverse culinary experiences, but you might be surprised to learn that it's also home to beautiful beaches along Lake Michigan. Don't miss the chance to relax and soak up the sun at one of Chicago's stunning beachfronts.
A Chicago suburbs photographer, Kathia A. Photography, says "My favorite activities include tasting Chicago; I am a big foodie person and I love trying different foods from different local restaurants. I also love doing a beach day during the summer. Nothing beats going to the beach and enjoying the summer weather right by the lake. It's a fun activity for the whole family."
8. Catch a show
Explore Chicago's vibrant cultural scene by visiting one of its renowned theaters or art centers, where you can watch a captivating performance, exhibitions, and artistic expressions that showcase the city's rich cultural heritage.
“It is difficult to pinpoint my favorite thing in DuPage County,” says Deborah Venezia from DuPage Foundation, an organization focused on fostering philanthropy, facilitating connections between donors and local needs, and addressing various issues to enhance a social impact.
“Filled with award-winning restaurants, world-class art exhibits, Broadway-caliber theater productions, and plenty of green space, it offers opportunities for all kinds of activities. Elmhurst Art Museum, the McAninch Arts Center, and Drury Lane Theatre, feature programming in visual and performing arts.”
9. Visit an arts center
Abbie, a newborn photographer known as Abbie Christine Photography, shares “I love to start a beautiful autumn day with a walk through Lincoln Park Zoo and North Avenue Pier. Green City Market in Lincoln Park is the perfect farmer’s market to meet up with friends and enjoy a warm beverage and freshly made bagel. It’s impossible to come home without a beautiful bouquet and fresh produce.
I also enjoy visiting the Chicago Art Institute with my family. The Ryan Learning Center located within the museum’s Modern Wing is always free to the public. The RLC has many activities for people of all ages – to create, look, touch, and experience art. Activities are inspired by current collections such as the Thorne Miniature Rooms. When we are done exploring in the RLC, we enjoy browsing through the galleries. As members, we enjoy taking advantage of the members' lounge for a complimentary cup of coffee or tea and a sweet treat for our daughter. From the member’s lounge, you can take the Nichols Bridgeway to Millennium Park.”
10. Join a running group
Lucas Larson, General Manager and Head Coach of the Heartbreak Hill Running Company, located in Chicago, says, “We host a group long run every Saturday morning, and the go-to spot for post-run brunch is Chicago Bagel Authority on Armitage. Their menu is enormous and even offers gluten-free and vegetarian options."
11. Rooftop bar crawls
Mike McMains, an expert tour guide who weaves together history, architecture, urban planning, and many other topics, better known as Tours With Mike, suggests, “Chicago is the country's architectural capital, and a great way to see a ton of beautiful design (with a drink in hand) is to go on a downtown rooftop bar crawl. My favorite stops are Cindy's at the Chicago Athletic Association, Cerise at the Virgin Hotel, and the rooftop at the LondonHouse.
Chicago is filled with incredible museums, including boutique ones off the beaten path. I always enjoy checking out the Driehaus Museum's gorgeous collection of Tiffany Studios stained glass, The Intuit's amazing collection of outsider art, and the one-of-a-kind International Museum of Surgical Science.
One of my favorite free things to do is exploring the Chicago Cultural Center. It has an eclectic mix of galleries with rotating exhibitions, free concerts and events, the Buddy store with its interesting offerings from local artists, and absolutely stunning stained glass domes designed by Tiffany Studios.”
12. Half Acre Brewery
Experience the thrill of conquering challenging bike routes through Chicago's bustling streets, soaking in the urban scenery as you pedal your way through the city's diverse neighborhoods. Cap off your adventure with a refreshing stop at one of Chicago's renowned breweries, where you can unwind and toast to your accomplishment with a cold craft beer.
“Our favorite thing to do is to ride our bikes to Half Acre Brewery,” says Kassi Cork, President of Half Acre Cycling, a local team that competes in cyclocross, road, gravel, track, and mountain biking.
“They have a delicious hop water on tap that is super refreshing after a long ride. Our other favorite thing to do is drink coffee at one of the Dark Matter cafes as we are obsessed with their deliciously strong coffee. For anyone interested in getting a bike or getting their bikes tuned up, we recommend the Bike Lane Chicago and Tailwind Cycles.”
13. Deep dish pizza
"Of all the special things about Chicago, the food really is the best,” says Leanne Founder of You Name it Events, local event planner and organizer. ”My favorite foodie adventure in Chicago is grabbing some deep dish sausage or pepperoni pizza from Pequod's Pizza on Clybourn and then walking over to Sweet Mandy B's on Webster for dessert. Pequod's deep dish has the best caramelized cheese on their crust that is unlike any other deep dish around. Sweet Mandy B's has a wide selection of sweets and treats that feel like they're homemade. Can't be this delicious combo of spots that are just a few blocks from each other.”
Chicago boasts a vibrant culinary scene with diverse restaurants offering a tantalizing array of cuisines from around the world, ensuring there's something to satisfy every palate.
14. Lake Michigan
The best part of Chicago is Lake Michigan,” mentions Sally, also known as Sally O'Donnell Photography. “I love to go to Promontory Point to swim as soon as the water is warm enough. June through September, we spent warm afternoons picnicking by the lake.”
Take a refreshing dip in the crystal-clear waters of Lake Michigan, where Chicago's stunning skyline provides a breathtaking backdrop for a day of swimming and relaxation. Promontory Point, nestled along the lakefront, offers a serene escape with its sandy shores and tranquil waters, making it the perfect spot to soak up the sun and enjoy a refreshing swim. Whether you're seeking a peaceful retreat or an active day by the water, Lake Michigan and Promontory Point offer unparalleled opportunities to unwind and connect with nature in the heart of the city.
15. Grab Pho
Big Day Photo & Video, local wedding photographer and videographer, recommends, “One of my favorite activities in Chicago is exploring the diverse culinary scene, and one highlight for me is indulging in Pho Loan on W Argyle St. Chicago's Argyle Street is renowned for its vibrant Vietnamese community and authentic Vietnamese cuisine.
The pho here is unparalleled, with rich, flavorful broth and fresh, aromatic ingredients. What makes it unique is not only the delicious taste but also the immersive experience of dining in this culturally rich neighborhood. Chicago is known for its diverse food offerings, and exploring the pho soup scene on W Argyle St is a must for any food lover looking to experience the city's culinary diversity.”
16. Highland Park and Botanical Gardens
Vanessa Schilling from Spidermonkey Cycling shares, “We ride in a group which makes it safer and some of our favorite routes include riding up to Highland Park and riding to the beautiful Botanical Gardens. Some of the highlights include riding past Northwestern University campus and the amazing Bahai Temple.
We meet for our rides at Hexe Coffee which has a great outdoor space and unbelievable baked goods. Once we get back in the city, we stop for a well-deserved traditional Chicago dog at Budacki's. Occasionally, we ride south to Willow Springs and stop for some tasty beers at Goose Island Brewery in the city on our way home.
Another favorite activity is riding on the Des Plaines River Trail. The whole ride is along the river which is very scenic and you can ride all the way to the Wisconsin border. All of these are great rides, but it's the people in Chicago that make them exceptional.”
17. Restaurant hop
Ashley, local lifestyle blogger of And That's Just Ashley, mentions, "One of my favorite activities is checking out the different restaurants Chicago has to offer. From hidden gems to the city's hottest new spots, I love exploring and experiencing different cuisines. Chicago is a top city for foodies – and for good reason. It truly has so much to offer to satisfy every palate and craving."
18. Garfield Park
“My favorite activity is running through the beauty of Garfield Park,” recommends Jackie Hoffman, Founder & Executive Director of Peace Runners 773, an inspiring non-profit organization that advocates for health equity. “My favorite route usually takes me past the Garfield Park Conservatory and the beautiful and historical Gold Dome, both staples of our community. The best time for this route is during the weekends because the Peace Runners Run Club are the mobile flowers that light up the area. After a run, I go to the conservatory to grab a drink from Momentum Coffee. They have the best turmeric ginger chai tea latte there. Nothing is better than a great drink while enjoying one of the best conservatories in the world.
19. Events in the city
Amanda Whitfield, Founder of Windy City Cosmo, shares, “Chicago's vibrant cocktail scene and networking opportunities inspired me to start my blog, reflecting the city's diverse dining experiences and global connections.
Chicago throws some epic events. I’ve probably been to over 500 events in the nine years I’ve been blogging. Have you been to Chicago Gourmet in Millennium Park? It’s a foodie’s dream as you take sips of inventive cocktails. Or simply just taking in the Old Town Art Fair and being able to walk through the exhibits and sit down as neighbors open up their secret gardens and patios. I’ve never seen anything like it in a big city.
She continues, “Chicago has good food. It just does and it delivers on ambience. From chucking an ice cube shot at Federales; savoring the service and inventive dishes at Girl & The Goat; enjoying a heavenly latte at the French cafe, Venteux; sharing a Peking Duck right outside of Asia on Argyle; or being whisked away by the waiter at The Aviary to the speakeasy, The Office, where you can literally sip on historic spirits in what feels like a man cave – every place kind of has its specialty, ya know? If I want a vibe, like sit and feel like you’ve been taken to another world — Beatnik West Town makes me feel like I’m in a jungle. Three Dots and a Dash makes me feel like I got off a cruise ship at night. BLVD makes me feel so sophisticated—like I found a hidden gem. They have cake and milk on the menu – and yes, you should get it.”
20. Thrifting
"My favorite Chicago activities are taking walks up Milwaukee Ave in Wicker Park, indulging in some thrift shopping, hopping between bars, and catching comedy shows with my friends,” mentions Carly Kazmer from the The Den Theatre, a Chicago hub for entertainment and artistic expression.
Thrift shopping in Chicago offers a treasure trove of unique finds, from vintage clothing and accessories to one-of-a-kind home decor items. With an array of thrift stores scattered throughout the city, exploring Chicago's thrift scene promises exciting discoveries and the chance to uncover hidden gems at affordable prices.
21. West Chicago activities
“If you’re staying on the west side of Chicago, there are a few staples you have to check out. My ideal day in Chicago starts with brunch at Spinning J Bakery and Soda Bar in Humboldt Park with some of our favorite food in the city (rated best pie by Good Morning America),” recommends Nathan Weil from The Humboldt Jungle.
After that, take a stroll up California to Adam and Son’s plant nursery, Vintage Quest, and Humboldt House. When you’re done shopping, go to Garfield Park Conservatory, it’s the best indoor plant conservatory in the country, but make sure you reserve your slot ahead of time.
After that, be sure to head up to Logan Square for dinner at Lula Café, a staple in the restaurant community with some of the best eats in the city. When you’re done eating, the last thing is catching a show at The Humboldt Jungle (a speakeasy house show in Humboldt Park) that offers stand-up comedy showcases and concerts with Chicago’s premier artists, you will be blown away in the room. Make sure you get tickets online as shows usually sell out ahead of time..”