Where to stay in Chicago when you want luxury that’s as bold as the city itself? The Peninsula Chicago. It’s not cheap—think Michelin stars over deep-dish pizza—but it’s impeccable. With skyline views, a rooftop spa, and service so flawless, you’ll feel like Al Capone without the legal trouble.
Welcome to the Windy City, a place where deep-dish pizza is practically a religion and every block seems to have something exciting going on!
But before you dive headfirst into exploring, you need a great place to stay.
Lucky for you, I’ve narrowed down the top 5 hotels in Chicago, so you can rest easy after a day of sightseeing, eating, and pretending not to be scared of heights at the Willis Tower.
Whether you’re booking a flight for a quick weekend getaway or planning an extended stay to fully immerse yourself in the city’s vibes, these hotels will make sure your trip is unforgettable.
Let’s get into it!
1. The Peninsula Chicago
The Peninsula is pure luxury. Think: spa treatments, jaw-dropping views, and one of the fanciest rooftops you’ve ever sipped a cocktail on.
Located in the Magnificent Mile, this spot puts you right in the middle of all the action—shopping, dining, and sights are just steps away. The service here? Top-notch. You’ll feel like royalty from the moment you step inside. Check rates here.
Pro tip: If you’ve spent too much time indulging in deep-dish pizza (which, let’s be honest, is likely), their wellness center is perfect for working off those extra slices.
2. The Langham, Chicago
If you’re all about sleek, modern design with a side of relaxation, The Langham is calling your name.
Situated right along the Chicago River, this beauty offers killer views and a soothing vibe that’ll make you forget all about the hustle and bustle below. Want to unwind? Head to the Chuan Spa. Feeling fancy? Afternoon tea is an absolute must. Check rates here.
Bonus points: You can basically wave at kayakers from your window. How cool is that?
3. Hotel Zachary, Chicago, A Tribute Portfolio Hotel
Calling all sports fans! Hotel Zachary is right across the street from Wrigley Field, so if you’re here to catch a Cubs game, it doesn’t get more convenient than this.
Even if baseball isn’t your thing, this boutique hotel is seriously charming with a cozy, neighborhood feel. The rooms are stylish, the food scene around Wrigleyville is solid, and let’s not forget—you’ll have endless stories to tell about the buzz around the stadium. Check rates here.
P.S. This is the perfect place to stay if you want to avoid downtown but still enjoy easy access to the city.
4. Chicago Athletic Association Hotel
Don’t be fooled by the name—this is not your average sports club. The Chicago Athletic Association Hotel is all about that old-school, classic vibe. Think leather chairs, dark wood, and grand ceilings.
Plus, the rooftop bar, Cindy’s, gives you some of the best views of Millennium Park (hello, Instagram moments!). Oh, and speaking of food, their in-house burger joint, Shake Shack, might just become your new favorite pit stop. Check rates here.
Pro tip: After wandering Millennium Park, Cindy’s is perfect for sunset cocktails. Trust me, the view is worth it.
5. The Emily Hotel Chicago
Looking for a trendy, creative atmosphere? The Emily Hotel, located in the West Loop, is where cool kids (and their dogs) stay.
It’s got an artsy vibe, with local artists’ work scattered throughout the space, and it’s pet-friendly—so bring your furry travel buddy along! The rooftop lounge is a hit for casual cocktails, and the neighborhood is packed with incredible restaurants and bars. Plus, you’re close enough to downtown to make it convenient, but far enough to enjoy some peace and quiet. Check rates here.
This is the place to stay if you want to explore Chicago’s food scene—especially if you’re all about trying new and off-the-beaten-path spots.
Final Thoughts
Whether you’re here for the Cubs, the deep-dish, or the skyline views, Chicago’s got the perfect hotel for you.
The only thing left to do is book your stay and start planning your adventures. Oh, and don’t forget to book a flight (unless you’re lucky enough to live close by—then we’re all a little jealous!). Each of these hotels offers a unique taste of Chicago’s personality, so take your pick and get ready for an epic trip.
From stunning rooftop views to iconic locations, this city never disappoints—and your stay won’t either.