We asked our 65k Chicago-loving followers what they thought were absolute must-dos for any visitor to the city.
Here’s what they said
1. The Architecture Boat Tour
This one came up again and again.
Even locals take it multiple times and say it never gets old.
The tour gives you great views of the city while you learn about Chicago’s rich architectural history.
Go with Chicago Architecture Center’s “Chicago’s First Lady” tour. It leaves from the riverwalk near the DuSable Bridge.
The tour guides are informative and funny, and there’s a bar on the boat if you want a drink.
Here’s a tip: try to get there 30 minutes early if you want a seat on the side of the boat. Sitting in the middle is fine too, but the side views are better. If you can, book an evening tour. The lighted buildings at night are stunning. One visitor said even their teenagers were into it, which tells you something.
The tour takes about 90 minutes, though there’s a 45-minute option if you’re short on time.
Keep in mind, during the Summer it can get hot during the day, so morning or evening tours are your best bet in summer.
2. Get Out of Downtown
Chicago is a city of neighborhoods, and you’ll miss a lot if you stick to the Loop and River North.
Lincoln Park, Old Town, Wicker Park, Andersonville, and Logan Square all have great dive bars, restaurants, and local shops.
Pick a neighborhood, find a local coffee shop that isn’t Starbucks, and wander around.
Andersonville has tons of character. Check out Uncharted Books, Lost Larson Coffee and Bakery, and the Wooly Mammoth curiosity shop.
The Swedish-American Museum is there too if you want something cultural.
Wicker Park and Logan Square are good for a younger crowd with lots of craft breweries tucked into the neighborhoods. Some have tap rooms where you can bring in food and play games.
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3. The Lakefront
Lake Michigan is beautiful. You can rent bikes from REI or Divvy and ride the lakefront trail.
The trail goes for miles in both directions, so you can make it as long or short as you want.
North Avenue Beach and Oak Street Beach are crowded but have great skyline views. Montrose Beach is more chill and better for picnicking.
There’s also a bird sanctuary at Montrose that’s worth checking out. Foster Beach up in Uptown is underrated.
If it’s hot out, the lake is refreshing. The water stays pretty cold even in summer, but it feels amazing when it’s sweltering. And if you’re feeling adventurous, you can even kayak on the river, though some people say it’s a bit scary.
Promontory Point in Hyde Park is another favorite spot for lake views, along with the little beach just south of Adler Planetarium.
4. Museums (Even if you don’t like museums)
The Art Institute is world-class. Even if you’re not into art, you should go. One person said it’s fantastic even for people who don’t usually like museums, and that’s a pretty strong endorsement.
The Museum of Science and Industry is another favorite. You can tour a WW2 submarine – you actually go inside it, which is a cool experience. The museum itself is huge, so plan to spend a few hours there.
The Field Museum is good for natural history. The Shedd Aquarium is decent, but people were split on it. Some said it’s not up to par with other aquariums they’ve visited. The Adler Planetarium is currently pretty minimal in terms of exhibits, with several closed, so you might want to skip it for now.
Consider getting a CityPass if you’re doing multiple museums. It saves money and lets you skip some ticket lines, which is helpful on busy days.
5. Water Taxi to Chinatown
For $10, you can take the water taxi down to Chinatown.
It’s a nice way to see the city from the water without committing to the full architecture tour.
Spend some time eating dim sum and hanging out at Ping Tom Memorial Park. The views of the skyline down the river are gorgeous. The park has beautiful willow trees and fun paths to walk.
After, grab drinks at Ninebar. Or if you want an amazing Asian steakhouse experience with wagyu by the ounce, try Holu. After exploring, you can take the red line back up to the Loop area instead of the water taxi if you want to see more of the city.
6. All The Food
Get thin crust pizza at Flo and Santos if you’re downtown – they have a great patio where you can sit outside if it’s not too hot.
For deep dish, try Lou Malnati’s with the butter crust or Pequod’s. Giordano’s is another option that gets mentioned a lot.
Chicago-style hot dogs are a must. You’ll find them all over the city.
Head up to Argyle on the red line and pick any restaurant – they’re all good for Vietnamese food. If you’re there on a Thursday, check out the night market. Just skip Tank Noodle – locals say it’s not ethical.
For Mexican food, go to Pilsen. On Devon, try Little India – Ghareeb Nawaz got a specific mention. Girl and the Goat, Duck Duck Goat, The Duck Inn, and Rose Mary all came up as excellent dinner options.
Russian Tea Time and Topolobampo are good for something different. And if you’re up at 3am (hey, it happens), hit Golden Apple.
Billy Goat Tavern on Michigan Avenue is a bit of a cliche, but the food is actually good. Do-Rite Donuts is great too – sign up on their website with your phone number and you might get a free donut. The location in Sears Tower has excellent cold brew.
7. Catch A Show
If you like comedy, get tickets for Second City.
It’s not too expensive and you might see future comedy stars. IO is another good improv spot.
Green Mill is great if you like jazz – locals have been going there for decades. Friday happy hour with the organ playing is a favorite. If you’re in the area, check out Foster Beach too.
Navy Pier does free fireworks on Wednesdays at 9pm and Saturdays at 10pm. But here’s the trick: don’t watch from Navy Pier. Go to Adler Planetarium instead. You’ll get the fireworks AND the best skyline view. Watching from Navy Pier itself can be underwhelming.
Chicago Magic Lounge is worth checking out. People say it’s worth paying extra for the more private show after the first one.
8. ….More Beautiful Architecture
If you really love architecture, there’s more to see.
The Driehaus Museum in River North is beautiful.
The Frank Lloyd Wright Home and Studio is in Oak Park – take the green line and you can walk there. You can also see a bunch of his other houses in the neighborhood. Unity Temple is there too.
If you happen to be visiting in autumn, Open House Chicago is amazing. Even if you can’t make it for that, their website has a list of past sites that you can visit at other times of the year.
9. Find A Roof With A View
The Up Room has one of the best views of Chicago, especially at dusk. Bonus points on Wednesday or Saturday when you can see the Navy Pier fireworks in the distance.
For rooftop bars, try London House at night for outstanding views. Cindy’s has a nice view too – you don’t need to eat there (it’s expensive), just grab a drink or even an iced tea and enjoy the patio.
For speakeasies, check out The Gatsby in Lincoln Park, Izakaya in Fulton Market, or Blind Barber in Fulton Market. These are good for nights when you’re willing to spend a bit more.
Smart Planning Tips
Start making dinner reservations 6-8 weeks in advance for popular spots.
Make multiple reservations for the same day if you need to, then cancel as your plans firm up. Keep checking – reservations open up as people cancel.
Get a 7-day Ventra pass and take the L or bus everywhere. It’s easy and saves money. The public transportation system is pretty straightforward once you get the hang of it.
Check Millennium Park for their summer music and dance series. They’re free and a great way to end your day. Pack a picnic or grab takeout nearby. There are also free movies in the parks – you can google the lineup. Bring a blanket and a bottle of wine.
Lincoln Park Zoo is free and worth a stroll. The conservatory and rookery are right next to it.
If you’re into baseball, catch a Cubs game at Wrigley Field. Get the cheapest tickets since the team isn’t great right now – the park itself is the real attraction. It’s a classic.
A Few More Neighborhood Suggestions
Fulton Market and the West Loop have great restaurants and fancy bars. It’s where a lot of the trendy dining is happening right now.
Hyde Park is pretty far south, but if you make it down there, Promontory Point and Washington Square Park are beautiful. The park has gorgeous willow trees.
The 606 Trail is good for a morning walk near Humboldt Park. Stop at Dayglow for coffee right off the trail.
What to Skip
Navy Pier itself is skippable unless you have kids who really want to go. The view is fine, but there are better ways to spend your time.
