If you’re excited about an upcoming trip to the Windy City but aren’t totally convinced you’ll be blown away, perhaps it’s time to create a travel bucket list.
Jump ahead to these sections:
- Unique Chicago Bucket List Ideas for Locals
- Must-Do Chicago Bucket List Ideas for Visitors
- Chicago Bucket List Ideas for Spring or Summer
- Chicago Bucket List Ideas for Fall or Winter
- Bucket List Foods and Restaurants in Chicago
- Bucket List Bars in Chicago
Sure, exploring on your own without a plan is great, but it’s nice to know there will be a few friendly pizzas and famous paintings awaiting you.
This post will help you plan your visit to Chicago, especially if it's on your bucket list. If you’ve already been, and you’re hoping for some fresh ideas for where to go, be sure to keep reading, too.
This post will cover more than 33 of the essential bucket list ideas in Chicago, including food and activities, as well as unique options for locals, what to do in different seasons, and more.
Unique Chicago Bucket List Ideas for Locals
Your travel bucket list doesn’t have to take you out of the country, out of your state, or even out of your city. If you’re a Chicago local who wants to explore a bit more, be sure to check out the following spots.
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1. Garfield Park Conservatory
If you wish you could escape to a lush, tropical climate but just can’t afford it right now, Garfield Park Conservatory may quickly become your sanctuary. It has several indoor gardens, an outdoor public garden, and artful plant arrangements that change every year.
2. Green Mill Jazz Club
Visited by Al Capone so much he had a favorite booth, this cash-only cocktail lounge could become a favorite of yours, too. Be sure to get there early enough, as it closes at 1:11 a.m.
3. Chicago Temple
With a unique history and an even more unique appearance, the Chicago Temple is a sight to behold. It’s the tallest church in the world, and it houses the city’s oldest church, the First United Methodist Church of Chicago. You can worship in the Sky Chapel (closest to the Gothic spire) a few times per week or enjoy a free tour.
4. Palmer House Hilton
How many people can say they’ve visited the place that invented the brownie? This Hilton is perhaps the perfect spot for the lavish staycation you know you’ve didn’t know you needed.
5. The Chicago French Market
If your weeknight dinner menu needs a little extra love, or you have a free weekend and want to do some browsing, check out Chicago’s French Market. This market offers more than 30 local vendors featuring the best of Chicago’s melting pot.
Must-Do Chicago Bucket List Ideas for Visitors
Visitors to Chicago should be sure to soak up the following sights. But fair warning, you might just enjoy them enough to become a resident.
6. Shopping on The Magnificent Mile
There isn’t just shopping with some of the world’s best retailers on Chicago’s Magnificent Mile—there’s also plenty of great food and other entertainment, too. Visit spots ranging from flagships to luxury department stores and boutiques, plus gourmet eateries and grocery stores.
7. Millennium Park
Millennium Park, Grant Park, the Art Institute, the Field Museum, and Shedd Aquarium have all made this bucket list. And believe it or not, they’re all right next to each other.
But don’t think that if you see it once you’ve seen it all—these spots cover a lot of land. Millennium Park, in particular, covers more than 20 acres and features the ever-popular, always charming sculpture, Cloud Gate, a.k.a. “The Bean.”
8. The Art Institute
The Art Institute is incredible, plain and simple. You’ll see renowned works (much like the cast of Ferris Bueller’s Day Off) from Van Gogh, Monet, and Renoir. And, if you don’t care for impressionists as much, explore hundreds of thousands of other works.
9. Skydeck Chicago
Located in the 110-story Willis Tower, the second-tallest building in North America, Skydeck Chicago is undoubtedly a must-see. If this seems a bit too high, though, you can experience Chicago from above (but nine floors lower) at the 360 CHICAGO Observation Deck.
10. The Second City
With shows every night of the week and on weekends, you’ll never be short on laughs. This famous improv theater (though there are multiple locations) has helped produce some of the best names in comedy, including Tina Fey, Bill Murray, Keegan-Michael Key, Steve Carell, and Steven Colbert.
Chicago Bucket List Ideas for Spring or Summer
In spring and summer, it’s best to take advantage of a few hotspots around Chicago while the weather is still in your favor—especially if you’re not used to the cold.
11. Grant Park and Buckingham Fountain
Grant Park in itself is beautiful, but Buckingham Fountain is particularly impressive, as it’s one of the largest fountains in the world.
12. Navy Pier
Great for families or the young-at-heart, Chicago’s Navy Pier offers a Ferris wheel, carousel, mini-golf, a children’s museum, and plenty of other attractions. Those of age can also fill up at the Miller Lite Beer Garden.
13. Chicago Architecture River Cruise
For fresh air, fun facts, and photo-ops, a Chicago Architecture River Cruise is a can’t-miss in the spring or summer, especially on a nice day.
14. Wrigley Field
Cubs fan or not, it’s always incredible to experience baseball at one of America’s most iconic ballparks—also featured in Ferris Bueller’s Day Off. Built in 1914, you’ll taste a bit of history along with your hot dog. If you’re unable to land tickets to a game during your visit, you can also tour the park.
15. The Morton Arboretum
The Morton Arboretum combines the beauty of nature and art. It’s the perfect escape for families or anyone who loves the urban wilderness.
Chicago Bucket List Ideas for Fall or Winter
When the weather turns a bit cold (or really, really cold), you can still authentically enjoy Chicago. Check out the following spots in Chicago during fall or winter.
16. The Field Museum of Natural History
This museum offers more than 40 million artifacts and specimens, so if you have hours to kill and want to be warm or away from the weather while doing it, do it here. That said, the Field Museum’s location on the shore of Lake Michigan makes it a beautiful spot for a picnic or to get some fresh air, too. You’ll enjoy an immersive experience of both nature and culture, and it’s great for all ages.
17. Ice Skating at Millenium Park
Millenium may have already made an appearance once on this list, but it’s worth mentioning again that you can still enjoy it in the winter.
18. Northerly Island
Enjoy a winter wonderland and snowshoe along the shores of Lake Michigan at Northerly Island, which is actually a manufactured peninsula. This is a great option for those who like to experience a bit of nature without losing sight of the city.
19. Soldier Field and Soldier Field Sledding Hill
Football fans and snow fans can unite at Soldier Field, home of “Da Bears.” If you’re visiting in the fall, try to catch some tickets to a game. Check out the 33-foot slope for sledding if you're visiting in the winter.
20. Shedd Aquarium
As one of the world’s largest indoor aquariums, Shedd Aquarium houses more than 32,000 sea creatures who want to stay out of the cold, too. This aquarium isn’t short on variety or interactivity, either, with stingrays ready for petting, as well as up-close encounters with penguins, turtles, belugas, and more.
Bucket List Foods and Restaurants in Chicago
Though you likely think of hot dogs and pizza, Chicago has a lot of variety around every corner. Stop and smell the air every once in a while, and your nose might just lead you somewhere special.
You can also check out some tips on making a food bucket list that expands beyond just one city.
21. Lou Malnati’s
Whether you’re team deep-dish, thin-crust, gluten-free, or crustless, Lou Malnati’s has tons of delicious pizzas to please everyone in your party. They also offer salads, appetizers, and other dishes to share.
There are 59 Lou Malnati’s locations across Illinois, as well as several others across the U.S. Of course, you’re sure to get the most authentic slices right in its birthplace of Chicago.
22. Stan’s Donuts
Another excellent option for gluten-free travelers is Chicago’s own Stan’s Donuts, which has plenty of delicious treats for everyone. Many of their popular flavors—like blueberry, pistachio, and chocolate glazed—come in gluten-free varieties. Stan’s also offers other great breakfast options, as well as cookies and coffee you can enjoy on the go or in-store. Look out for Stan’s mobile truck, too!
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23. Garrett’s Popcorn
For popcorn lovers or fans of all things salty and sweet, another Chicago original, Garrett’s Popcorn shops, are a can’t-miss. Started by a female entrepreneur in her family’s kitchen, this popcorn is still made fresh daily. You can smell it all over the city near any of their locations.
Popular flavors include the classic Garrett Mix, which is their caramel popcorn mixed with their world-famous cheddar, as well as others like Buttery, Plain, and Macadamia CaramelCrisp. And, if you get hooked while you’re visiting, you can have their popcorn shipped across the U.S. and Canada.
24. The Original Pancake House
You’ve heard of the International House of Pancakes, but Chicago will do you one better with The Original Pancake House. It may not be a Chicago original (it began in Portland, Oregon), but it’s still worth a visit. Menus vary by location, but offerings include apple pancakes, Dutch Babies, omelets, crepes, eggs benedict, waffles, and many others.
25. The Purple Pig
If you’re looking for a swankier spot and “cheese, swine, and wine” sounds more like your speed, the Purple Pig is a great spot. It was voted one of the “10 Best New Restaurants in America” by Bon Appétit, and it offers rustic, sharable plates filled with fresh ingredients inspired by the flavors of Italy, Greece, and Spain.
26. The Dearborn
With brunch, lunch, dinner, dessert, and drink options, this tavern is a great escape any time of day, any time of year. The décor features murals of Chicago history as well as cozy leather booths.
According to Eater, Soulé “amps up soul food classics like nourishing shrimp and grits, jerk chicken wings, and blackened catfish”—it’s the bit of soul you need if the wind in the Windy City gets a bit too cold.
28. Dolo Restaurant and Bar
Perfect for groups of friends, families, or dates, Dolo offers made-to-order dim sum with a twist, thanks to Cajun flavors and other surprises.
29. Superdawg Drive-In
If you have a car and you’re craving a Chicago “dawg,” Superdawg is your spot. While you’re sure to find plenty of other street vendors or restaurants serving them (and plenty of other grilled meats and veggies), Superdawg’s retro delivery is worth witnessing.
Bucket List Bars in Chicago
Grab your buds. The following bars are some of the best Chicago has to offer. You can also add any of these to your itinerary as a starting point and just see where the night (or day) takes you.
30. The Rainbo Club
Basically unchanged since the 1940s, the Rainbo Club offers an authentic tavern experience—plus a man selling $6 bags of tamales if you get hungry. Be advised that this bar gets packed on weekends.
31. Sportsman’s Club
With a cozy interior filled with taxidermy or a sprawling outdoor patio that attracts top chefs for cookouts in the summer, the Sportsman’s Club is a great spot to bring the boys, gals, whomever.
32. The Violet Hour
This posh speakeasy encourages limited phone usage—but you won’t miss them. You’ll likely be enthralled by their inventive and classic cocktail menu.
33. The Office
A perfect option for the indecisive ones in your group, this cozy speakeasy is both discreet and offers what’s called “the dealer’s choice.” You simply describe your tastes and preferences per the bartender’s questions, and they’ll make you something from scratch.
Wind Up in the Windy City
From museums, parks, shopping, and food, the Windy City is no doubt a winning destination that everyone should visit at least once in their life. And for those who live there, perhaps it’s time to explore it like new all over again. You may also be interested in this guide on how to make a travel bucket list.