
Hotel vacation 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.
Vacation rentals for every style
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Popular amenities for Chicago Loop hotel rentals
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!

2BD/2BA w/ gourmet kitchen, private balcony & more
Best stay we have had in Chicago. Loved the rooftop and having a garage to park in. The place was spacious and the beds were comfortable ☺️

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

Your Oak Brook Escape| Free Parking & Pet-friendly
It was a very convenient location for the airport with many restaurants and shopping centers around. The room was very clean and comfortable as well. Highly recommended.

Close To Chicago O'Hare Airport | Free Breakfast
everything was nice 😊

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.

Comfort and Relaxation! Parking, Near Navy Pier
Clean hotel, beautiful room and area. Lots in walkable distance and friendly staff! Already at looking at coming back.

modern design with VU Skyward rooftop bar
I arrived earlier than my booking time and they were available to get me a room. It was right across the street from the event I was going to as well.

Sparkling clean and quiet hotel!
This Air B&B is in the Radisson. it is an older hotel but very clean. There was a party going on in the lobby but we never heard a sound from our hotel room. The room was very clean. The bed was very comfortable. there was a fridge which was larger than what you usually see in hotel rooms. All in all, very nice and well worth the price.

King Bed with breakfast included
perfect for a night’s stay. will definitely book again.

Prime River North Location! Pool, Rooftop Deck
Rooms were nice, TV worked, beds were just as in picture. The only thing was there was no rooftop access from the elevators or stairs as it was listed to be available. So I'm not sure if it's only accessible from the main lobby room or just not available anymore.
Quick stats about hotel rentals in Chicago Loop
Total rentals
220 properties
Nightly prices starting at
G$4,184 GYD 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
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
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- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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