Alright so if it’s your first time in Chicago, you’re probably feeling a lil bit overwhelmed with all the stuff to do. Totally get it. This city’s got sky-high views, wild food, cool neighborhoods, and tons of museums. You could spend a week here and still feel like you missed something.
I put together this guide to help you hit all the good spots without stressing over what’s actually worth your time. Some of it’s classic tourist stuff (cuz yeah, some of that is actually awesome).
If you’re tryna see a bunch of the big attractions, might wanna look into that Chicago CityPASS too. it covers several spots and saves you a few bucks along the way.
If you’re still sorting your hotel, check out the top rated Chicago hotels by neighborhood. I also put together a 3-day itinerary if you’d rather not piece everything together yourself. And if you’re here to eat, don’t sleep on these fun food tours.
Take an Architecture River Cruise
So one thing you definitely gotta do in Chicago is hop on one of those boat tours down the river. You basically just glide along while the guides tell cool stories about all the famous buildings and skyscrapers you pass. These tours last around 60-90 minutes, and honestly it’s the best way to see some super iconic buildings like Tribune Tower, Willis Tower, and those corn-coby Marina City towers.
Tours run every day from spring through fall. Plus, their boats have roofs, so you won’t get soaked even if the weather decides to be annoying. Snag tickets early to lock in the timing you want, so you can plan other activities around it.
Quick tip: Book the morning tour if you want nice lighting and fewer crowds. But honestly, a lot of locals swear the sunset tours are the best which isn’t surprising. Definitely bring your camera because you’ll get some good skyline pics you just can’t get from the street.
Oh and also, most boats let you bring snacks and drinks on board, so pack some stuff and make it a chill little river cruise.
Try The Iconic Deep Dish Pizza
If it’s your first time in Chicago, you gotta try deep dish pizza. It’s literally an inch-thick crust piled up with cheese, sauce, and toppings. Honestly, it’s more like a Chicago tradition than just pizza.
A go-to favorite is Lou Malnati’s, mostly cause of their buttery crust and chunky tomato sauce. Pequod’s is worth hitting up too, their crust has this caramelized cheese on the edges that gets all crispy. Giordano’s is solid but just a heads up, it’s usually full of tourists.
And if you want to sample multiple great spots at once, just join a pizza tour and you will get to try more than the typical Chicago Deep Dish pizza.
Here’s the thing if you are DIY-ing it, deep dish pizzas take like 45 minutes to bake, so don’t show up super hungry at 7 PM on a Saturday unless waiting forever sounds fun. Way easier to call ahead or order online.
Quick note, always eat deep dish with a knife and fork. Don’t try folding it like you’re in New York, you’ll probably get funny looks.
Local tip: Go to Lou Malnati’s in River North during weekday lunch. They have these smaller, personal-sized pizzas that cook faster, and you’ll totally skip all the dinner crowds.
Take a Food Tour Through Chicago’s Diverse Neighborhoods
Chicago definitely has way more going on food-wise than just deep-dish and hot dogs (even though they’re pretty great). If you wanna get a good feel for the city, a walking food tour is your best bet. It lets you try out a bunch of spots in just a few hours, plus you learn some cool neighborhood stories along the way.
Most people usually kick things off downtown, since that’s where you’ll get a taste of all the classics like deep-dish slices, Chicago-style dogs (remember, never ketchup), maybe some craft beer, and brownies. It’s a good starting point if you’re new in town and trying to hit all the must-eats.
But if classic Chicago foods aren’t totally your thing, there’s other options too. Some popular theme-specific tours focus on sweet stuff like donuts, taking you to spots locals swear by, but tourists don’t usually know about.
It’s a chill way to see the city, try foods you probably wouldn’t find on your own, and just makes exploring Chicago way more fun.
Visit Millennium Park and “The Bean”
Okay so Millennium Park is legit one of the best spots to check out in Chicago. You HAVE to see the giant shiny Bean. Official name is Cloud Gate but literally no one calls it that. Everyone just says the Bean. If you don’t already know, it’s basically this huge mirror sculpture reflecting the Chicago skyline and everyone standing around looking up at it. Probably the most Instagrammed thing in the entire city honestly.
Little advice, just go super early or kinda late at night if you don’t want a billion selfie sticks in your photos.
Getting there is super easy too. Just hop on the L and jump off at Millennium Station. I’d say plan like an hour just to wander around, snap a ton of pics, and do some people-watching. The park has other fun stuff too, like Crown Fountain where these giant faces spit water out and kids run around laughing like crazy. It’s pretty fun to watch.
Oh, and here’s a little secret tip: the Bean looks AMAZING right at sunrise. City lights still twinkling, sky turning pinkish-orange, and the reflection hits different. Totally worth waking up early.
Check Out The Magnificent Mile
Michigan Avenue is that super famous shopping street everyone calls the Magnificent Mile. It runs from the Chicago River all the way up to Oak Street and it’s packed with shopping spots from luxury to international brands.
But don’t forget to look up sometimes, cause the buildings along here are beautiful. There’s the Gothic-style Tribune Tower and that super white Wrigley Building everyone takes pictures of. And definitely check out the Historic Water Tower, one of the only buildings that actually made it through the Great Chicago Fire in 1871.
If you’re bringing kids, they’ll probably flip over the LEGO store or American Girl Place. Or just chill for a bit inside Water Tower Place, it’s basically an eight-story mall in the middle of everything.
You probably wanna set aside a couple hours at least to see everything. I’d start around DuSable Bridge cause that’s where the views of the skyline are really good, then just walk north from there. If you’re trying to dodge big crowds, show up right when shops open around 10 AM, cause weekends get packed.
To get some of the best views in the city, you can hit up the 360 CHICAGO Observation Deck. And when you need a coffee break, there’s a Starbucks Reserve Roastery here.
Sunset At Willis Tower Skydeck
There’s several buildings in Chicago where you can go up for some nice city views. One of them is the Willis Tower with a Skydeck that’s over 1,300 feet above the streets.
The coolest part here is The Ledge. It’s basically these glass boxes that stick out from the 103rd floor, so when you step out onto them you feel like you’re just floating in the air above Chicago. Kinda scary, but super cool. People go nuts for selfies there, obviously.
The tower’s right downtown, super close to Union Station so it’s easy to walk over. It’s open daily from 9 AM to 10 PM. Give yourself like an hour or so to wander around, check out the little exhibits and stuff, and obviously get those pics on The Ledge.
Pro tip: Head up before sunset to watch the color changes, then stay to see Chicago’s glittering nighttime landscape. Also grab your tickets early so you don’t spend time queueing and miss the golden hour!
Stroll Along The Chicago Riverwalk
The Chicago Riverwalk is this super pretty path that runs about a mile and a quarter right along the river downtown. It goes from Lake Shore Drive all the way over to Lake Street, and has some of the best city views. Tons of locals come down here just to hang out, grab food at outdoor cafes, or watch the boats going by.
The path itself is kinda split up into different sections, or “rooms,” each with a different feel. Some areas are quiet spots where people even fish sometimes, and others are more lively with great views of all the tour boats passing by.
If you wanna do something different, you can even rent a kayak from Urban Kayaks and paddle around yourself. Or better yet, join one of their guided kayak tours. It’s pretty cool seeing Chicago from water level.
See if you can visit around sunset (especially if you didn’t do the boat tour during sunset), the buildings make these nice golden reflections on the water, and all the restaurants along here turn on their twinkly lights. It’s a whole other vibe.
Visit the Field Museum of Natural History
If you’re into dinosaurs or like, cool old stuff in general, you gotta go to the Field Museum. It’s one of those places that kinda blows your mind with how much is packed inside. The main star is SUE the T. rex. Biggest and most complete one ever found.
The museum’s down on Museum Campus, right by the lake. Super easy to get to if you’re already checking out that area. You’ll need at least a couple hours. There’s plenty to see, from ancient Egypt stuff to exhibits on cultures from all over the world.
Best move is to get your tickets online ahead of time so you’re not stuck in line with a bunch of other tourists. Or if you’re planning to hit up a few other spots in the city, grabbing a CityPASS is a pretty decent deal.
Wednesdays in the morning are usually less packed, so if you can swing it, go then. And if you don’t wanna pay museum café prices for food that’s kinda meh, pack your own lunch and chill out in the South Garden. It’s peaceful and you get lake views while you eat.
Oh and definitely check out the free daily tours they do. They’ll take you through the highlights so you don’t miss the cool stuff.
Hang Out At Navy Pier Attractions
Navy Pier sticks way out into Lake Michigan and is loaded up with stuff to do for pretty much everyone. Yeah, some locals will call it touristy but whatever, the views of the skyline from here are amazing, especially from the top of that huge 200-foot Centennial Wheel.
The pier stays open pretty late, till around 8 PM most weekdays, and until 10 PM on Fridays and Saturdays. If you’re trying to dodge big crowds, the trick is to hit it up early on a weekday or go during the quieter months when it’s not peak tourist season.
Summer nights at the pier are kind of a vibe though. They have free fireworks shows twice a week (Wednesdays at 9 PM and Saturdays at 10 PM). But you’ll wanna skip the crowded pier and catch the fireworks from spots like Polk Bros Park or Milton Lee Olive Park nearby. Way less packed and still great views.
Other than the wheel, there’s a bunch of other cool stuff too. You’ve got the Chicago Children’s Museum if you’re bringing kids, Crystal Gardens (this indoor garden that’s pretty nice for a quick walk-through), and plenty of seasonal events year-round.
Lots of locals aren’t huge fans of the sit-down restaurants here as they’re kinda overpriced. But I guess the food court’s fine if you just want something quick while looking out over the lake.
Secret Tip: See if you can grab a drink at Offshore Rooftop. It’s the world’s largest rooftop bar, right on top of the pier, and you get pretty much the same killer views without feeling like a total tourist.
More Highlights And Tips For Chicago
Honestly, this is just scratching the surface of what Chicago’s got going on. There’s way more to see, eat, and do depending on what you’re into. Whether you’re here for the architecture, the food, the views, or just wanna wander around and see what you stumble into, you won’t be running out of things to do.
If you’re still planning your trip or just wanna dig a little deeper, we’ve got more recs waiting. Go take a peek at the other guides for more ideas. Chicago’s not going anywhere!
