13 Best Hotels in Chicago in 2023, According to Travel Experts

While the weather in Chicago is generally most comfortable in late spring and fall, summer doesn’t usually get terribly hot. The average high temperature in July and August is the low 80s and there’s usually a decent breeze. Of course, it’s more crowded during the summer months, especially during the Lollapalooza music festival (the first week of August). Cicero visited in mid-August while the Chicago Air and Water Show was happening and didn’t find crowds to be much of an issue. Still, many attractions require or recommend advance reservations, so it’s a good idea to plan out at least some of your trip.

As for those who dare to brave Chicago winters, don’t forget your coat, hat, gloves and winter boots, and beware that while the hotels and airfare may be cheaper, the temperature is often below freezing, the winds can be fierce and there is certainly no lack of snow due to the lake effect.

To create this list, the Good Housekeeping Institute experts have researched dozens of the best hotels, read through hundreds of five-star reviews and have personally stayed at many of the picks featured on this list. We’ve also included top picks our GH testers have traveled to. We evaluate each property on a variety of factors, including location, price, staff, comfort, cleanliness, amenities and more. We also consider feedback from online reviewers when picking our top properties.

You could spend a month or more in Chicago and not run out of fun things to do. Families may want to prioritize the Shedd Aquarium (the winner of a Good Housekeeping 2023 Family Travel Award) and if there’s a dino fan on the trip, the Field Museum. “Since these two attractions are next to each, plan to spend the entire day in the area,” said Cicero, who visited with her family last summer. “Buy lunch from a food truck, and eat it in the grassy area. Running around outside for a while will help prevent museum fatigue.” The Museum of Science and Industry is also packed with exhibits that will appeal to school-age kids and up. “We spent a half-day there, but could have stayed longer,” said Cicero. Another family-friendly — and free — gem in the city is the Lincoln Park Zoo. “Based on the variety of animals and how well you’re able to see them, the zoo is one of the best we’ve ever visited,” noted Cicero.

All-ages fun includes a River Cruise Architecture Tour (It’s even better after dark when the buildings are lit up!) and
Millennium Park (Snap a selfie in front of the famous Bean.). Artsy visitors may want to buy tickets to one of the Broadway in Chicago shows and meander in the galleries of the Art Institute of Chicago. The Riverwalk is particularly lovely during warm days when you can take in views of the Chicago river and stop in a restaurant or bar to relax. You may even recognize it from pictures on social media of the green river during Chicago’s Saint Patrick’s day festivities.
While touristy, the Chicago Skydeck, which lets you walk above the skyscraper, is fun. Ditto for Navy Pier, which merits a one-time visit for a spin on the 200-foot Ferris Wheel.

If you’re in the mood for shopping, the Magnificent Mile features well-known stores like Nordstrom’s, Anthropologie and the holy grail for doll-obsessed kids, American Girl Place. The Andersonville section of town is dotted with secondhand shops, comic-book stores and vinyl record stores. It’s not far from the home of the Chicago Cubs, Wrigley Field. “My teen daughter, who doesn’t usually watch baseball, had a blast seeing an afternoon game,” said Cicero. “She rooted for ‘The Cubbies’ for the rest of the season.” Of course, no trip to Chicago is complete without exploring the bustling nightlife and tasting some of their iconic cuisine, like a Chicago-style deep-dish pizza or a Chicago Italian beef sandwich.