Chicago Travel Guide: My Favorite Places to Eat, Stay & Explore
Chicago is one of those cities I keep finding my way back to. I’ve visited for family vacations, New Year’s Eve trips, concerts and work—and I even spent a summer living in the suburbs during an internship. At this point, I’ve honestly lost count of how many times I’ve been!
So instead of a typical weekend itinerary, I’m rounding up my favorite Chicago finds from over the years—from iconic stops and places to eat to hidden gems, unique stays and things you might not find on every Chicago guide.
Whether it’s your first visit or your tenth, there’s always something new to discover in Chicago.
Navy Pier
Walking around Navy Pier is one of those classic Chicago activities that’s worth doing at least once! It’s free to explore, and I love simply walking along the water, watching the boats go by—and honestly, doing a little people watching too. Ride the Centennial Wheel for views over the city and Lake Michigan, and check the event calendar because there’s often live music or something else happening around the pier. You can also hop on one of the boat tours that depart from here if you want to get out on the water. It’s an easy stop to spend as little or as much time at as you want.
360 CHICAGO
We visited 360 CHICAGO during a family trip in December and loved seeing the city from above! The observation deck has incredible views of the Chicago skyline and Lake Michigan, and a few of our family members added on TILT, which literally tilts you out over the city—they all loved it! There’s also CloudBar at the top where you can grab coffee or an adult beverage while taking in the views. Definitely worth adding to your itinerary, especially if you’re visiting Chicago with family.
Millennium Park & Cloud Gate
No trip to Chicago is complete without a walk through Millennium Park and a stop at Cloud Gate—better known as “The Bean.” It’s a classic Chicago photo stop, but take some time to walk around the surrounding park too. There’s something happening throughout the year, from outdoor events in warmer months to ice skating nearby during the winter, making it worth visiting in any season.
Wendella Architecture Tour
We absolutely loved this experience! Hop aboard a Wendella boat for a sunset architecture tour along the Chicago River and take in some of the best views of the city while learning about its iconic buildings. It’s relaxing but still such a fun way to experience Chicago, and there’s even a full-service bar on board if you want to grab a drink for the ride.
Museum of Ice Cream
If all-you-can-eat ice cream sounds like your kind of activity, add the Museum of Ice Cream to your Chicago list! I had previously visited the San Francisco location and knew I wanted to check out Chicago’s with my family. You’ll make your way through colorful, interactive rooms while sampling plenty of ice cream along the way—including some fun flavors beyond your typical chocolate and vanilla. The sprinkle pool was easily the hit of our visit and makes for some pretty fun photos too! This is a great indoor activity for families, couples, or anyone with a serious sweet tooth.
The Field Museum
You could easily spend several hours exploring the Field Museum, with exhibits spread across multiple floors covering everything from dinosaurs and ancient civilizations to the natural world. My favorite was obviously seeing SUE the T. rex and learning more about the dinosaurs, but I also loved exploring the Ancient Egypt exhibit and seeing the mummies. There’s so much to see here, and it’s a great Chicago activity for families too!
Ghirardelli Chocolate
I’m a sucker for chocolate, so of course a stop at Ghirardelli had to make the Chicago list! You can pick up chocolates to take home or treat yourself to sundaes, shakes, hot chocolate and other desserts. I’m personally a big fan of anything caramel and chocolate! If you’re visiting Chicago during the winter, this is an especially cozy stop to warm up with a hot chocolate after walking around the city.
Explore Chicago’s Chinatown
Chinatown is one of my favorite neighborhoods to simply walk around, explore and eat your way through! There are tons of restaurants, shops and bakeries to check out, with everything from hot pot and Korean BBQ to dumplings and more. My favorite stop is the popular Qing Xiang Yuan Dumplings, where you can actually watch the dumplings being made—definitely make a reservation if you can because it gets busy!
Kennedy Rooftop
I’ve been to Kennedy Rooftop a few times now because we really love the vibe here! Since it’s in Wicker Park rather than downtown, you get a great view looking back toward the Chicago skyline. Grab a cocktail or something to eat and enjoy the rooftop, or head inside if the weather isn’t cooperating. It’s a fun spot for drinks with a view without being right in the middle of downtown.
Beatnik on the River
Beatnik on the River is easily one of the prettiest places to dine in Chicago. The eclectic space is decorated from floor to ceiling, and its location right along the Chicago River makes the views hard to beat. I stopped in specifically for happy hour and loved the fattoush salad and handmade fries. Between the atmosphere, waterfront setting, and food, it’s a great spot for happy hour, date night, a girls’ night out, or grabbing a bite with coworkers after work.
Nan Xiang Soup Dumplings
If you love soup dumplings, Nan Xiang Xiao Long Bao is definitely worth adding to your Chicago list. They’re known for their Shanghai-style soup dumplings and even offer a colorful Lucky Six sampler if you want to try several varieties. I went with the black Truffle & Pork Soup Dumplings, which were packed with flavor and one of my favorites of the meal.
We also tried the cucumbers, noodles, shrimp and several other dumplings, and honestly, it was hard to go wrong with anything we ordered. The menu is especially great for sharing, so I’d recommend coming with friends or family and ordering a bunch of dishes for the table. The Chicago location is right in River North, making it an easy stop to add to a day exploring downtown.
Lucca Osteria & Bar
Lucca Osteria & Bar is a great upscale dining option in the Chicago suburbs, whether you’re planning a date night or looking for somewhere nice to meet while traveling for work. I had to order the fettuccine, which is finished tableside in a giant cheese wheel and is just as fun to watch as it is to eat! I also tried one of their cocktails topped with a bubble, which made the whole experience feel a little extra. Between the elevated atmosphere, cocktails and memorable pasta presentation, this is definitely a spot I’d return to in Oak Brook.
Park Beer Garden
1S151 Winfield Rd, Wheaton, IL 60189
For a cozy fall activity outside of downtown Chicago, head to the Beer Garden at Cantigny Park in Wheaton! I spent some time walking through the beautiful park and gardens before grabbing a beer and pizza and listening to live music outside. It was such a relaxing way to spend an evening after work, especially once the fall weather started rolling in. I went solo, but this would be a great casual date night or a fun spot to meet up with coworkers after work.
After more trips to Chicago than I can count, I still feel like I’ve barely scratched the surface. That’s one of my favorite things about this city—there’s always another neighborhood to explore, restaurant to try, hidden gem to find, or reason to come back.
And since I’m still making my way back to Chicago regularly, this guide isn’t finished. I’ll continue adding new finds as I experience them, so save this one for the next time you’re planning a trip to the Windy City!
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