Chicago Travel Guide – How to Have The Most Unique Weekend in Chicago
August 11, 2021 |
By Danielle Dudek
weekend in chicago

Before we begin, we need to point out that this post focuses on unique, off the beaten path ideas for things to do and see during a weekend in Chicago. If you are looking for more touristy type things like Grant Park, Sears Tower (aka Willis Tower), Magnificent Miles, etc., check out Choose Chicago.

Because we’ve been to the Windy City many times, this trip was all about trying new things. So, without further adieu…

Here’s how to spend a unique weekend in Chicago!

Friday –

We flew into Midway and then headed directly to the West Loop neighborhood. Here you will find the awesomely instagrammable WNDR Museum. Chicago’s first immersive experience, the museum is constantly changing. Hopefully, when you visit it will still include Chicago’s first-ever Infinity Mirror Room by iconic Japanese artist Yayoi Kusama.

WNDR Museum
1130 West Monroe Street

After snapping all the pics at the museum, you’re going to need to fuel up for the remainder of the evening. What better food choice for your first night in Chicago than PIZZA?! We could dedicate many a post to the debate about who has the best pizza but we’re not going to go there. Whether you like deep dish, thin crust, or even a style made famous in another city, you’ll find it in every neighborhood. I’ll dare to share my personal favorites though: Pizano’s and Aurelio’s Pizza.

Chicago Pizza

Ready for more picture perfect locales? There’s no shortage of filming locations in and around the city – if you are interested in seeing things like that in real life. Here are a few of our faves. Another thing there seems to be no shortage of is TV show and movie inspired pop-ups.

Check out Replay Chicago and see what they currently have going on. At the time of our visit, the Lincoln Park location was paying homage to “The Office.” Here are a few pictures to give you a better idea of the experience.

Replay Lincoln Park
2833 N. Sheffield

After all that adventure, it’s probably time to call it a night. Located right in the heart of Magnificent Mile, we spent our first night at DoubleTree by Hilton where there’s a full array of amenities including an on-site restaurant, bar, and rooftop pool.

Saturday –

Day two started with brunch at AO Hawaiian Hideout. The newest and hottest HAWAIIAN-inspired restaurant in Chicago’s South Loop, this hidden tropical gem features a luau brunch with an Elvis tribute band. We’re all shook up just remembering how much fun it was!

AO Hawaiian Hideout
1315 S. Wabash Avenue

Since you’re already on the South side, try to hit up a White Sox game. If you’re really lucky, you may be in town when they host their annual Elvis night. If you’d rather see the Cubs play, make your way up to Wrigleyville on the L. There’s plenty to do and see in that area, even if there isn’t a game.

Another option is to head out of the city and check out one of the neighboring communities. Nearby towns we recommend include Evanston, Wilmette (home to the only Taj Mahal-style temple in the US), Riverside, and Highland Park. The latter is where you’ll find many John Hughes movie filming locations and was once home to Michael Jordan and currently home to Billy Corgan of the Smashing Pumpkins.

On this trip, we traveled out to Oak Park which is famous as the hometown of Ernest Hemingway. It’s also where Frank Lloyd Wright spent much of his early career. You can wander the neighborhood near his studio to see multiple FLW designed and inspired homes.

Back in the city, you may want to hit another pop-up because, as previously mentioned, there’s no shortage of special exhibits and events in the Windy City. The Friends Experience was definitely a highlight – though sadly it has closed.

Before heading to dinner and drinks, check out the 21c Museum Gallery. 21c Museum offers unprecedented access to the work of some of today’s emerging artists, every day all day. It’s free and open to the public 365 days of the year. And here’s something really cool: you can sleep there! That’s right. We had a legit night at the museum. While the first two floors are filled with modern art, the upper floors contain stylish and comfortable hotel rooms. Learn more about how you can book your stay here.

Since you’re right in the middle of downtown, there’s no shortage of spots to eat and drink. No matter which way you turn, you’ll likely find a fun place to park yourself for the evening. We wandered over to Hubbard Street and found the picture perfect JoJo’s Shake Bar, El Hefe, and O’Callaghan’s Irish Pub.

Sunday –

Before heading to Midway (where you can fly back to Austin direct on Southwest), brunch was most definitely in order. Just around the block from 21C is Goddess and the Baker. Their website states that they are an energetic gathering place with good food, fun treats, and excellent coffee. We can attest to all of that. Try the iced brown sugar cold foam latte. Not only is it tastier than the brown sugar latte at Starbucks, it’s cheaper! They have a multitude of really creative and yummy coffee drinks. Check them out here. The food choices are just as delightful. And make sure you save room for dessert! Their cakes and cookie are to die for. Yes, that’s key lime cake baked into an actual lime!

Well, there you have it. The perfect way to spend three perfect days in Chicago! Of course, if you have more time than what’s outlined, there are many many many more things to do.

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