
Hotel holiday rentals in Chicago Loop
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Top-rated hotel rentals in Chicago Loop
Guests agree: these hotel rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for hotel rentals in Chicago Loop
Family-friendly hotel rentals

Spacious 2BR near concert venues, Wrigley Field
Rick’s place was great. Everything matched the photos. Location was great. Easy access to transportation if needed. Concierge was very helpful and friendly as well. Would stay here over and over again

Vibrant Andersonville 2BR w/ in-unit laundry
This place was perfect for a week in Chicago with family! The space was as described, beautiful and sparkling clean, and communication with the host/staff was quick and easy. Having a 24-hour concierge and sundries for sale in the lobby was fantastic for any questions or snack/drink needs. And the Andersonville neighborhood is such a fun place to explore, with lots of great restaurants and shops!

Bright 1BR w/ shared Roof Deck, close to beach
FANTASTIC Andersonville place to stay, walkable to all the best the neighborhood has to offer! Rick is super responsive, helpful, kind, and generous! Highly recommended, and hope to return soon :)

1BD/1BA steps away from local shops, entertainment
A wonderful place, clean, well equipped, friendly, and located in a great neighborhood. We will return the next time we go to Chicago!
Hotel rentals with a pool

Close To Chicago O'Hare Airport | Free Breakfast
Great location, good breakfast and close to the airport. 100% Recommended

120-yr-old landmark with floor-to-ceiling views
The location is amazing! Extremely walkable to the lake & the river. So many places to eat & shop nearby. This room is a Superior king room, which isn’t noted in the listing, so look it up on their website; where you may even get a better rate and choose the type of room you’d prefer. It is quite small @337sq ft, even for just 2 people, but a nice room nonetheless. There is no dresser, just a closet with 2 smaller drawers, which worked ok for us. Full size lighted mirror, a shower & soaking tub (!!!) The pillows were all down feather or like.They did have water stations on 3 of the floors to fill your bottles, a great feature. The rooftop bar had delicious tapas and craft cocktails and a beautiful view of the city and lake. Paid $386 a night at the end of August & Labor Day wknd. The staff were extremely friendly. Overall, we enjoyed our stay very much! Would def stay again, but would book through Viceroy directly and get a lake view room that is larger.

Guest room with 2 Double Beds + PET Friendly
The room given to us was amazing. The bed was like a cloud, it was so comfortable. We felt welcomed coming into the room! I will definitely be coming back.

modern design with VU Skyward rooftop bar
I would recommend Hilton Garden Inn as a good place to stay in Chicago, and would consider staying again. The employees were friendly and helpful. The rooms were spacious and clean overall. The only downside is there isn't a complimentary breakfast, but there are plenty of options in the hotel and surrounding for various places like Starbucks downstairs. I did try the hotel Breakfast on the 22nd floor, and it was a pleasant experience. The waitress was very friendly, there is a lovely view of the lake and surrounding city, plus the food was fresh and tasty.

Guest king Room at Aloft Chicago Mag Mile
This was a great place for a great deal! The location is perfect and the hosts were so helpful and responsive.

King Bed with breakfast included
Stayed the night after a family function. Didn't arrive until midnight but was super glad that we were able to check in so late, as someone is at the front desk. It was easy to find. Room was larger than expected. Bed was very comfortable and room was clean. The only minor issue we had was noise from people hanging out in the parking lot/being loud, outside our window, past midnight. Luckily it didn't go on too long, and we were able to sleep. We planned on breakfast, but choose to get the extra sleep in the AM instead, so we skipped it. All around would def not hesitate to book again.
Quick stats about hotel rentals in Chicago Loop
Total rentals
220 properties
Nightly prices starting at
£15 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
20 properties have a pool
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- Six Flags Great America
- Museum of Science and Industry
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Willis Tower
- Skokie Country Club
- Garfield Park Conservatory
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Odyssey Fun World
- Flossmoor Golf Club
- Moraine Hills State Park
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