
Hotel holiday rentals in Chicago
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Top-rated hotels in Chicago
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Superhost

Hotel room in Uptown
4.91 out of 5 average rating, 35 reviewsSpacious 2BR near concert venues, Wrigley Field
tatiannaRating, 5 stars8 months ago
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
Superhost

Hotel room in Uptown
4.85 out of 5 average rating, 20 reviewsVibrant Andersonville 2BR w/ in-unit laundry
CourtneyRating, 5 stars81 months ago
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!
Superhost

Hotel room in Uptown
4.98 out of 5 average rating, 44 reviewsBright 1BR w/ shared Roof Deck, close to beach
TylerRating, 5 stars28 months ago
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 :)
Superhost

Hotel room in Andersonville
4.67 out of 5 average rating, 6 reviews1BD/1BA steps away from local shops, entertainment
SusanRating, 5 stars32 months ago
A wonderful place, clean, well equipped, friendly, and located in a great neighborhood. We will return the next time we go to Chicago!
Hotels with a pool

Hotel room in Rosemont
4.65 out of 5 average rating, 20 reviewsClose To Chicago O'Hare Airport | Free Breakfast
JavierRating, 5 stars3 weeks ago
Great location, good breakfast and close to the airport. 100% Recommended

Hotel room in Gold Coast
4.5 out of 5 average rating, 4 reviews120-yr-old landmark with floor-to-ceiling views
AndreaRating, 5 stars7 months ago
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.

Hotel room in Near South Side
4.58 out of 5 average rating, 26 reviewsmodern design with VU Skyward rooftop bar
IngridRating, 5 stars2 weeks ago
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.

Hotel room in Schaumburg
4 out of 5 average rating, 14 reviewsQuiet, clean, comfortable hotel
MarkusRating, 5 stars6 months ago
Having booked more than 40 people in this hotel/ air bnb, I highly recommend this place to any local people or travelers that are passing by. The price is unmatchable when compared to other hotels. Great customer service, and front desk staff, clean, friendly, and comfortable stay. Their staff also works 24/7 so don’t even worry if you come too late or early!

Hotel room in Schaumburg
4.64 out of 5 average rating, 11 reviewsSparkling clean and quiet hotel!
ClaireRating, 5 stars5 months ago
I was hesitant booking a hotel through Airbnb, but it was super easy, much cheaper and we had no issues.

Hotel room in Westmont
4.45 out of 5 average rating, 33 reviewsKing Bed with breakfast included
StephanieRating, 5 stars3 months ago
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
Total rentals
380 properties
Nightly prices starting at
$16 AUD before taxes and fees
Total number of reviews
6.4K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
150 properties allow pets
Rentals with a pool
40 properties have a pool
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- The Field Museum
- Lincoln Park Zoo
- Six Flags Great America
- Promontory Point
- Museum of Science and Industry
- Brookfield Zoo
- Humboldt Park
- Skokie Country Club
- Illinois Beach State Park
- 875 North Michigan Avenue
- Skydeck Chicago
- Splash Station
- Flossmoor Golf Club
- Villa Olivia
- Raging Waves Waterpark
- Moraine Hills State Park
- Lincoln Park
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