Last Updated: 12/24/23 | December 24th, 2023
Chicago is one of my favorite American cities. I love its striking architecture, sprawling green spaces, delicious food, and world-class museums. During the summertime, when the city comes alive after a very cold winter (it does get very cold here in the winter), I don’t think you’ll find a better city in the US!
And, as one of the biggest cities in the U.S., there’s no shortage of places to stay, regardless of your budget. And, with the city is big and spread out, you’ll want to make sure you stay close to the attractions you want to see.
I’ve been visiting Chicago for over fifteen years and have stayed in countless hotels. To help you choose a place to stay during your visit, here’s my list of the best hotels in Chicago (based on my experience):
1. Staypineapple
This fun hotel is located in the Loop, the center of Chicago. Staypineapple is in a landmarked historic building with beautiful mahogany-lined walls and furniture. While rooms are on the smaller side (which makes sense for such a central location), there’s everything you need for a cozy stay. All rooms have extra-fluffy duvets, oversized pillows, soft robes, blackout curtains, huge towels, Keurig coffee/tea makers, and unlimited bottled water. You’ll get a free welcome drink upon arrival at the attached bar/restaurant, which serves up great food from breakfast to late evening. There’s a fitness center and bike rentals available too.
2. 21c Museum Hotel
The neighborhood of River North has the highest concentration of galleries in the city, making it a great area to stay in if you like art. In fact, this hip property has a 24-hour contemporary art museum right on the premises. As for the rooms, they are sleekly stylish, huge, and filled with natural light. I found the beds quite comfy, with luxurious bedding. The bathrooms are big too, with upscale bath products and plush robes. The in-house eatery, Lure Fishbar, offers breakfast in the mornings and has one of the best burgers around.
3. Hotel Versey
Hotel Versey is located in Lakeview, a large, sprawling, and laid-back neighborhood. It sees few tourists but has great restaurants, chill bars, and vintage shops. This hotel has fun and funky décor, with murals and art in the hallways, lobby, and rooms. There’s exceptionally friendly staff, free Wi-Fi, and comfortable beds. In-room amenities include large flat screen TVs, desks, and phone docking stations. You also get free access to the LA Fitness gym right next-door (a super cool perk that I loved). While there’s no breakfast at the property, you can get discount vouchers for some nearby places at the front desk.
4. City Suites
City Suites is the ideal place to stay if you’re going to a game at Wrigley Field, as it’s less than a 15-minute walk away. The 45 colorful and cheery rooms are bedecked with tasteful Art Deco stylings and fully stocked mini fridges. It’s a great place for longer stays or while working on the road, as all rooms, while compact, have a desk and mini fridge. You’ll also get free access to a nearby fitness center. While there’s no breakfast on site, there’s free tea and coffee available 24/7 in the lobby.
5. Hyatt Place Chicago South
Hyatt Place is in leafy Hyde Park, a neighborhood that hugs up against the lake south of downtown. This three-star hotel boasts an indoor pool, fitness center, and a café on-site. Plus, it includes a complimentary continental breakfast, which is rarer than ever among hotels in Chicago in this price range. The rooms have a simple design but are spacious, and the bathrooms are good-sized too. All rooms are fitted with a pull-out sofa bed, desk, mini fridge, large flat screen TV, and free Wi-Fi.
6. Chicago South Loop Hotel
This upscale three-star hotel is in the Loop but close to Chinatown, you’ll have easy access to both neighborhoods when staying here. There’s a fitness center, pool, and a business center with free printing. While there’s no breakfast available at the hotel, there’s free parking, which isn’t common at such a centrally located hotel in Chicago. If you have a car, you’ll save a lot on parking! The spacious rooms have lots of natural light, extra comfortable queen-sized beds, and flat screen TVs. While the design and atmosphere isn’t anything particularly unique, I think it’s a great value for such a central location.
7. Sophy Hyde Park
Appropriately luxurious for the beautiful and historic Hyde Park neighborhood, smart, art-filled Sophy offers large, modern, and colorful rooms. All rooms in this boutique hotel have hardwood floors, love seats, ottomans, charging stations, blackout drapes, and 55-inch flat screen TVs. The marble tiled bathrooms all have a large walk-in shower, vanity, and luxury bath products as well. Downstairs, there’s a cozy library, a restaurant that serves both breakfast and dinner, and a cocktail lounge complete with an outdoor firepit seating area.
8. Westin Chicago River North
The upscale Westin is set right along the Chicago River in River North, one of my favorite areas to stay in. The rooms are bright and spacious, and some even have river and/or skyline views. All rooms feature a tea/coffee maker, desk, and a flat screen TV. There are even rooms that feature Peloton workout machines, though there’s also a fitness center to use as well. There are several restaurants on site too, including Kamehachi, the hotel’s very own sushi bar. I’ve stayed at a lot of Westins and this is one of the nicer ones!
There’s a huge variety of hotels in Chicago. Book one from the above list and start looking forward to your trip to one of the best cities in the country, knowing you’ve chosen a great place to stay.
Book Your Trip to Chicago: Logistical Tips and Tricks
Book Your Flight
Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:
Looking for the Best Companies to Save Money With?
Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.
Want More Information on Chicago?
Be sure to visit our robust destination guide on Chicago for even more planning tips!
