Posted: 12/14/23 | December 14th, 2023
Chicago is one of my favorite American cities. I love the striking architecture, sprawling green spaces, delicious food, and world-class museums. I think it’s one of the best cities, especially during the summer time. As one of the biggest cities in the U.S., there’s no shortage of places to stay. No matter your budget, there’s plenty of options. 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):
- Staypineapple
This fun, quirky, and friendly hotel has rooms with extra-fluffy duvets, oversized pillows, soft robes, and huge towels (everything you want in a hotel for a cozy stay). Rooms also have coffee, tea, and unlimited bottled water. It’s located in the Loop, the center of Chicago and home to some of the city’s best attractions, including Millennium Park and the Chicago Institute of Art. If you want to be able to walk to everything, stay here. Book here! - 21c Museum Hotel
The neighborhood of River North has the highest concentration of galleries in the city. It’s an awesome area if you like art, and 21c is the ideal hotel to stay in as this hip property is crammed with it. There’s a free contemporary art museum that’s open 24 hours on the premises. As for the rooms, they are all stylish, sleek, and comfortable. Plus, the in-house eatery, Lure Fishbar, has one of the best burgers around. Book here! - Hotel Versey
Hotel Versey has free Wi-Fi, large flatscreen TVs, phone docking stations, and friendly staff. It’s located in Lakeview, a large, sprawling district that, while quite far from the center of Chicago, is an extremely laid-back neighborhood that sees few tourists. Here you’ll find great restaurants, chill bars, and vintage shops. Within Lakeview lies the microneighborhood Wrigleyville, named after Wrigley Field, home to the Chicago Cubs, making this the best place to stay if you’re here for a game. Book here! - City Suites
Also located in Lakeview, the 45 colorful and cheery rooms at City Suites are bedecked with tasteful Art Deco stylings and have fully stocked mini bars. It’s a great place for longer stays or while working on the road, as all rooms have a desk and mini fridge, plus you’ll get free access to a nearby fitness center. There’s free 24/7 tea and coffee in the lobby too. Book here! - Hyatt Place Chicago South
Boasting an indoor pool, fitness center, and a café on-site, this three-star hotel includes a complimentary continental breakfast and each room is fitted with a pull-out sofa bed and large flatscreen TV. Hyatt Place is in leafy Hyde Park, a neighborhood that hugs up against the lake south of downtown. Book here! - Chicago South Loop Hotel
This upscale three-star hotel in the Loop offers a fitness center and spa as well as free parking. The spacious rooms all have extra comfortable queen-sized beds and flatscreen TVs. Located in the Loop but close to Chinatown, you’ll have easy access to both neighborhoods. Stay here to have both the city’s main attractions and delicious Chinese food close at hand. It’s a very affordable option for such a central location. Book here! - 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 flatscreen TVs. The marble tiled bathrooms all have a large walk-in shower, vanity, and luxury bath products as well. There’s a cozy library and restaurant downstairs too. Book here! - 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. Some rooms have river and/or skyline views. There are even rooms that feature Peloton workout machines, though there’s also a fitness center to use as well. There’s a coffee machine in every room and you can enjoy sushi at Kamehachi, the hotel’s very own sushi bar. Book here!
*** 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!