If you’re new to the Windy City and still figuring out what to do, this list’s gonna help you out big time. Chicago’s packed with cool spots and fun things to try, but it can get a little overwhelming if you don’t know where to start. Whether you’re just here for a few days or trying to see what all the hype’s about, this guide’s got a mix of everything to help you make the most out of your trip.
Planning a Trip to Chicago
If you’re in the middle of planning a couples’ getaway to Chicago, you’re in for something special. Once you’ve got your dates locked in, you might want to check out our full 3-day Chicago itinerary to help you pace your days in the city, especially if it’s your first visit. We’ve also rounded up some of the best classic things to do in Chicago that first-timers usually don’t want to miss. And if you haven’t settled on where to stay yet, our guide to Chicago hotels has picks for every style and budget.
Classic Chicago Experiences
Snap That Perfect Couple Shot At The Bean
If I’m gonna be real here, you haven’t really been to Chicago until you’ve taken that classic selfie at The Bean. This weird, funny sculpture is found in Millennium Park and it’s safe to say that it’s in everyone’s list, and honestly, I’m not even complaining cause it really deserves all the hype.
The Bean might be the park’s main draw, but once you guys are there, don’t just snap a photo and bounce. The park itself is a whole experience. From the playful Crown Fountain to the wide open lawn that’s perfect for relaxing, there’s plenty of space to slow down and just enjoy each other’s company.
If the weather’s good, you can grab coffee nearby, find a shady spot, and turn it into an easy date with your bae.
Cruise Along The Chicago River
You haven’t really done Chicago right if you skip the architecture cruise. It’s one of the city’s super popular experiences, like the Bean, but this one gives you a front-row seat to the city’s amazing skyline while cruising down the river. Super relaxing, scenic, and surprisingly enjoyable, especially if you’re visiting with your boo.
This one is a history and sightseeing cruise so this is more on the informative side. If you wanted something that’s more on romantic skyline cruising, you can switch this up to a sunset cruise on the river and lake michigan.
Both are extremely popular and fantastic to experience so just make sure to book your timed slots before your trip.
Take A Romantic Evening Stroll Down The Riverwalk
Speaking of Chicago River, The Chicago Riverwalk is another good spot for couples. The views here are amazing no matter which way you’re heading.
What makes this place even better is how there’s tons of restaurants and cafes tucked along the path. You can easily grab a table by the water and have dinner with the skyline right in front of you, or just stop for drinks and people-watch.
Once the sun starts to set and the lights come on, the whole place takes on a really cozy, romantic vibe you and your bae would enjoy. Definitely add this one on those spots you’ve gotta be during nighttime.
Try The Best Pizza in Chicago
Trying deep-dish pizza in Chicago is basically a rite of passage. It’s thick, cheesy, and ridiculously filling. Definitely something you’ll want to tackle together.
But here’s the thing though: while deep dish gets all the fame, locals will tell you that tavern-style pizza is where it’s at. It’s thinner, crispier, cut into squares, and honestly way easier to eat without needing a nap after.
If you’re both big on food adventures, make it a mission to try both styles and see which one wins. Lou Malnati’s and Giordano’s are the classics for deep dish. On the other hand, spots like Vito & Nick’s or Pat’s are where locals go for that crunchy tavern-style bite.
You can even take it up a notch and join a pizza tour that lets you taste your way through some of the city’s best slices. It’s a fun and casual date idea that’ll leave you full and maybe a little competitive about whose favorite was better.
Walk Down The Magnificent Mile
If you and bae love shopping or just wanna wander around the city together, then you 100% have to go to Mag Mile. Michigan Avenue stretches from the river up to Oak Street, and there’s always something to see here. It doesn’t really matter if you’re not really out to buy anything, it’s still fun to window shop and people-watch while you take in the city’s energy.
Be aware though that there’s gonna be a lot of people here so if you don’t really like dealing with all of that, try to go around early, right when the shops open, so the crowds are way lighter and it’s more peaceful.
And if you’re already in there, definitely check out the massive Starbucks Reserve Roastery. And maybe also swing by the Harry Potter store nearby if you’re a big fan.
Dress Up For A Broadway Show In The Theater District
Catching a Broadway show in Chicago is another classic date move, and it totally delivers. The Theater District has a few stunning venues, but if you’re going to pick just one, make it the Chicago Theatre.
If you’re into all those behind-the-scenes stuff, you guys can also check out the Chicago Theatre tour during the day. It gives you a peak at the history and lets you walk around the stage and dressing rooms. It’s another fun way to appreciate the space even more, especially if you’re catching a show later that evening.
Make a full night of it by grabbing dinner nearby before curtain time. There are a bunch of restaurants in the area, so it’s easy to find a spot that fits your vibe. And if you’re looking to save a bit, keep an eye out for rush or lottery tickets. Sometimes you can score amazing seats without blowing your budget.
Embrace The Tourist Magic At Navy Pier
I’ll confirm it. Navy Pier is 100% a tourist trap. But honestly, if you’re a tourist, why skip the touristy stuff?
You’re here to experience Chicago, right? So you might as well do it all, Ferris wheel and all.
The Centennial Wheel is one of those cheesy-but-fun things you and bae can try. The views from the top are actually pretty amazing, especially if you go around sunset. You get the city skyline on one side and the lake on the other.
Alternatively, you can just grab some snacks, and stroll along the water while listening to live music or random street performers.
But the real reason to stick around is the fireworks. If you’re visiting in the summer, they put on free shows every Wednesday and Saturday night. And this is where I actually think Navy Pier shines, so try to look for a good spot to see it and enjoy.
Sky-High Views
Step Out Over The City Together At Skydeck Chicago
It’s not every day you get to stand on top of one of the tallest buildings in the country, so go check out Skydeck at Willis Tower already!
The highlight here is The Ledge, those clear glass boxes that stick out from the side of the building. Stepping onto them feels like you’re floating over the city, and it’s a little scary at first, but it’s also gonna be really fun to do together. Most couples end up laughing through it, especially while trying to snap that perfect photo with the streets way down below.
It’s even better if you go right before sunset. Catch the golden hour glow, and then watch the city lights come to life while you’re both up there.
Important Tip: Definitely grab your tickets ahead online so you don’t waste time in line.
Experience The Thrills Of TILT At 360 Chicago
If you cannot handle the crowds at Willis Tower then 360 Chicago is definitely the perfect alternative for you.
It’s up on the 94th floor of the former John Hancock building, and honestly, some people even like it more than Willis Tower. You get a sweeping view of Lake Michigan, the skyline, and all the city lights, just without the long wait.
The big thrill here is the TILT, a ride that leans you out over the side of the building. It kinda sounds intense (it actually is 😂), but I’m pretty sure doing it with your bae would make it feel better. You’ll probably both be holding onto the rails and laughing the whole time.
After the adrenaline wears off, you can chill out at CloudBar, which is right at the top. It’s not the cheapest spot for a cocktail, but when you’re 94 floors up with the city glowing below, it’s hard to complain.
Since it’s pretty close to Navy Pier, you can easily pair this with dinner or a lakeside stroll without running all over town.
Outdoor & Nature
Wander Through Sea Life At Shedd Aquarium
You can never really go wrong with an aquarium date, and Shedd Aquarium definitely makes a strong case for it. It’s set right on Museum Campus by the lake, which already gives it bonus points for the views and walkability.
Inside, there’s a ton to explore. The Wild Reef is full of vibrant corals and sleek sharks swimming just inches away, and there’s something pretty mesmerizing about watching jellyfish drift around. The dolphin presentations are fun to catch too, and they give you a quick breather to sit and just enjoy the show.
But honestly, half the fun is simply strolling through the exhibits together, pointing out weird-looking fish, and getting excited when you spot something cool. The only downside here is it’s too popular so it’s always packed there so be sure to prepurchase your tickets online on their website to skip the long wait and queues outside.
Experience Urban Charm In Lincoln Park
Lincoln Park is definitely one of those spots you shouldn’t skip. It’s a great go-to if you’re looking for something chill away from the busy downton.You can spend hours here just walking around together, especially if you’re both into those unplanned, go-with-the-flow kinds of dates.
Definitely check out Lincoln Park Zoo. It’s free btw so no need to think much about the expenses, which is actually pretty rare for a zoo this good, and it has a lot of open spaces so it doesn’t feel cramped at all. Right next to it is the Lincoln Park Conservatory, full of tropical plants and flowers that’s honestly like a hidden gem tucked in the park.
After checking those out, follow the path all the way to North Avenue Beach. It’s the perfect place to relax, kick your shoes off, and wind down after spending a long afternoon of walking.
Unique Experiences & Activities
Hop On A Chicago Beer Tour
If you and your partner are into craft beer, a chicago brewery tour is a seriously fun way to spend an afternoon together. You’ll ride a barrel bus (very hippy btw, if you ask me lol) with an expert guide and visit three different local breweries across the city.
It’s easy, and you don’t have to worry about driving or figuring out directions. The whole thing is already mapped out, so all you need to do is show up ready to drink some really good beer. It’s definitely for the extroverts, since you might end up chatting with other couples or groups throughout the whole experience.
Tours run on selected days only, so it’s a good idea to book your tour slot in advance. Just make sure to eat a good meal beforehand and wear comfy shoes since you’ll be hopping on and off the bus a few times and sampling beers all afternoon.
Create Street Art Together At A Graffiti Workshop
If you’re looking for something a little different to do with your partner, a graffiti and street art workshop might be the perfect match for the two of you. This one’s for couples who wanted a totally unique experience that’s both fun and actually memorable. You’ll be able to team up with a local artist, learn some spray-painting techniques, and create your own custom piece of art together.
Everything’s provided, from the spray paint and gloves to the protective gear. At the end, you’ll actually have a cool canvas to take home as a souvenir from your trip.
Take A Couple Of Lessons In Magnificent Mile
If you’ve decided to stroll around the Magnificent Mile and want to do something a little different with your partner, there are a couple of niche classes nearby that are worth checking out. These are what I think are super fun date ideas that let you get creative together while trying something totally new.
Candle making classes are a hit among couples in the city. You’ll learn how to make your own candles from scratch, picking out scents and colors to suit your vibe. Most sessions last around two hours, and by the end, you’ll each have a few custom candles to bring home. It’s a cozy activity that’s perfect if the weather outside isn’t great.
If you’re more into fragrances, the perfume making class is another cool option. It’s surprisingly fun figuring out what smells you both gravitate toward. The instructors break it all down in a simple, engaging way so you actually learn something while doing it. And the best part? You both get to leave with custom perfumes that’ll always remind you of your trip together.
Fall in Love with Chicago
If you’re planning to squeeze in more stuff while you’re in the city, there’s a few other guides you might wanna check out. If you’re coming with kids next time, we’ve got a list of fun things to do in Chicago that’s perfect for the whole fam. For food lovers, there’s a bunch of awesome food tours that’ll take you to some underrated local spots. And if you’re the type who likes seeing all the famous sights, we’ve got you covered with a full guide to Chicago’s top landmarks too.
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