Holiday Rentals in Chicago
Find the holiday rentals that appeal to you the most
The 10 Best Holiday Rentals in Chicago, USA
Check out our pick of great holiday rentals in Chicago
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The Avondale Guesthouse
Chicago
Located in Chicago, 4.6 km from Wrigley Field and 5.5 km from Lincoln Park Zoo, The Avondale Guesthouse provides air-conditioned accommodation with a patio and free WiFi. This recently renovated holiday home is located 7.2 km from United Center and 8.1 km from 360 Chicago. On clear days, guests can head outside to enjoy the holiday home's outdoor fireplace or simply kick back and relax.
France
Great stay in a lovely little house, clean, well-decorated and very well-equipped. Close to local commerces and to north-south and east-west bus routes, and also to the river for walking or jogging away from the traffic. And next-door to a good Argentinian steak restaurant.
The Sono Chicago 3 stars
Old Town, Chicago
The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 1.2 km away. Parking is free with permit provided by The Sono Chicago.
The rooms are fitted with a flat-screen TV with premium cable channels. Each room has an en suite bathroom with a large shower.
Germany
The housekeeper was very friendly. The location is great: a more calm area but with the Chicago Elevated in walking distance. The breakfast is outstanding compared to US hotel standards in this price range. Rooms are comfortable and clean.
Ray's Bucktown Bed and Breakfast 3 stars
Bucktown, Chicago
Located near numerous restaurants and shops in the Bucktown neighbourhood of Chicago, Ray's Bucktown features a communal sauna, free WiFi, and in-room breakfast service. Live entertainment at the Congress Theatre is 800 metres away.
United States
Everything. The atmosphere, the staff, everything was incredible. I only wished I had stayed longer. Ashlee was very helpful and accommodating. I was upgraded to the room with a view and would highly recommend staying there.
Studio with private bath room
Hyde Park, Chicago
Set in Chicago, 1.4 km from 57th Street Beach, Studio with private bath room offers recently renovated accommodation with free WiFi and a garden. The air-conditioned accommodation is 2.4 km from 63rd Street Beach. The property is non-smoking and is located 1.2 km from Museum of Science and Industry - Chicago.
United States
Very comfortable, quaint and cozy and clean. I felt safe in the neighborhood. The worst part is that I only stayed 2 days. I hope this property is available for my next visit.
Fully Furnished Apts at The Mag mile -Cloud9 - 747
Magnificent Mile, Chicago
Fully Furnished Apts at The Mag mile -Cloud9 - 747 offers accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a microwave, a fridge and kitchenware. Less than 1 km from Oak Street Beach and a 17-minute walk from Ohio Street Beach, the property provides a rooftop pool and a garden. Private parking can be arranged at an extra charge.
United States
Exactly as pictured. Beautiful, comfortable and clean
Fully Furnished Apt Near Millenium Park- 29
Chicago Loop, Chicago
Fully Furnished Apt Near Millenium Park- 29 features accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave. 2.7 km from Ohio Street Beach and 400 metres from CIBC Theatre, the property offers a seasonal outdoor swimming pool and a garden. Private parking can be arranged at an extra charge.
United States
This property is at a great location. It is nice and roomy. The kitchen is all furnished. Both the unit and the public areas are clean and easy to access.
Cozy 2 brm apartment mins away from United Center
Chicago
Located in Chicago, 1.9 km from United Center and 5.1 km from Union Station, Cozy 2 brm apartment mins away from United Center offers air conditioning. Both free WiFi and parking on-site are available at the apartment free of charge. The property is non-smoking and is set 6.2 km from Millennium Station.
Czech Republic
Everything was clean and cozy, you’ll find everything you need - washing machine and dryer, hair dryer too, host was also really nice and prompt with respond
The Twin Lions: Bespoke Travel Lodge w/ Speakeasy*
Bucktown, Chicago
The Twin Lions: Bespoke Travel Lodge w/ Speakeasy* is a recently renovated apartment in Chicago, where guests can make the most of its garden and bar. Among the facilities at this property are a concierge service and room service, along with free WiFi throughout the property. The property is non-smoking and is set 3.4 km from Lincoln Park Zoo.
Zimbabwe
The whole place was so tastefully decorated. Everything you could need or want was there provided for you. The location was great and free parking out front made it very comfortable.
Chicago Charm
Chicago
Offering garden views, Chicago Charm is an accommodation set in Chicago, 11 km from Lincoln Park Zoo and 13 km from 360 Chicago. The air-conditioned accommodation is 2.6 km from Loyola University Chicago, and guests can benefit from private parking available on site and free WiFi. The property is non-smoking and is located 6.6 km from Wrigley Field.
Turkey
Every detail has been considered to make you feel at home. It has everything a house should have. The decoration is very nice and relaxing. The beds are comfortable. Sheets and towels are clean. Ventilation works well. It was fun to watch movies on the big screen TV. Wi-fi provides very fast internet. The location of the house is very close to the city. You can reach the city center in approximately 20 minutes by car. You can park your car in the private parking lot at the back. There is a seating area on the back balcony. Very useful in nice weather. If I go to Chicago again, I will definitely stay here.
Romantic 3 Bed Home In The Heart Of The Park
Chicago
Situated 6.2 km from Guaranteed Rate Field, 11 km from Art Institute of Chicago and 11 km from Field Museum of Natural History, Romantic 3 Bed Home In The Heart Of The Park features accommodation located in Chicago. The air-conditioned accommodation is 3.8 km from Museum of Science and Industry - Chicago, and guests can benefit from on-site private parking and complimentary WiFi. Adler Planetarium & Astronomy Museum is 11 km away and Willis Tower is 12 km from the holiday home.
United States
The property had a lot of space and the host was a good host.
Most booked hotels in Chicago in the past month
Popular with guests booking hotels in Chicago
8.9Scored 8.9FabulousRated fabulous· 1,124 reviews
Popular with guests booking hotels in Chicago
8.1Scored 8.1Very goodRated very good· 339 reviews
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8.5Scored 8.5Very goodRated very good· 264 reviews
Popular with guests booking hotels in Chicago
8.9Scored 8.9FabulousRated fabulous· 132 reviews
Popular with guests booking hotels in Chicago
8.5Scored 8.5Very goodRated very good· 501 reviews
Popular with guests booking hotels in Chicago
8.4Scored 8.4Very goodRated very good· 91 reviews
Popular with guests booking hotels in Chicago
8.4Scored 8.4Very goodRated very good· 70 reviews
Popular with guests booking hotels in Chicago
6.8Scored 6.8PleasantRated pleasant· 399 reviews
Popular with guests booking hotels in Chicago
9.5Scored 9.5ExceptionalRated exceptional· 276 reviews
Popular with guests booking hotels in Chicago
8.3Scored 8.3Very goodRated very good· 256 reviews
Chicago's best hotels with breakfast
Ray's Bucktown Bed and Breakfast
Hotel in ChicagoBreakfast options9.6Scored 9.6ExceptionalRated exceptional· 207 reviewsLocated near numerous restaurants and shops in the Bucktown neighbourhood of Chicago, Ray's Bucktown features a communal sauna, free WiFi, and in-room breakfast service.
Super unique and interesting plenty to do on and off property.
The Polo Inn Bridgeport U.S.A.
Hotel in Bridgeport, ChicagoBreakfast options9.4Scored 9.4SuperbRated superb· 66 reviewsJust 6 miles south of the Chicago city centre, this Bridgeport B&B is 3 minutes’ drive from U.S. Cellular Field, home of baseball’s White Sox.
It was cozy,charming and in such a perfect location.
The Avondale Guesthouse
Hotel in ChicagoBreakfast options9.3Scored 9.3SuperbRated superb· 121 reviewsLocated in Chicago, 4.6 km from Wrigley Field and 5.5 km from Lincoln Park Zoo, The Avondale Guesthouse provides air-conditioned accommodation with a patio and free WiFi.
i like the games,couches and smart tv with good inter
The Sono Chicago
Hotel in ChicagoBreakfast options9.5Scored 9.5ExceptionalRated exceptional· 276 reviewsThe Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 1.2 km away. Parking is free with permit provided by The Sono Chicago.
The flushing of toilet in next room was sometimes a bit of a bother
Studio with private bath room
Hotel in Hyde Park, ChicagoBreakfast options10.0Scored 10.0ExceptionalRated exceptional· 8 reviewsSet in Chicago, 1.4 km from 57th Street Beach, Studio with private bath room offers recently renovated accommodation with free WiFi and a garden.
The privacy, the silence. The neighborhood was very calm. It was close to the places I visited.
9.9Scored 9.9ExceptionalRated exceptional· 7 reviewsFully Furnished Apts at The Mag mile -Cloud9 - 747 offers accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a microwave, a fridge and kitchenware.
Exactly as pictured. Beautiful, comfortable and clean
9.8Scored 9.8ExceptionalRated exceptional· 11 reviewsFully Furnished Apt Near Millenium Park- 29 features accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.
Great location. Easy to book. Clean and 24 hour security
Cozy 2 brm apartment mins away from United Center
Hotel in ChicagoBreakfast options9.3Scored 9.3SuperbRated superb· 11 reviewsLocated in Chicago, 1.9 km from United Center and 5.1 km from Union Station, Cozy 2 brm apartment mins away from United Center offers air conditioning.
It was so beautiful and comfortable I didn’t want to leave 🥰
Sentral Michigan Avenue
Hotel in South Loop, ChicagoFree cancellation options available8.9Scored 8.9FabulousRated fabulous· 1,124 reviewsSentral Michigan Avenue offers accommodation within 1.8 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.
Very nice room, great kitchen. And there was everything you needed.
Sonder Jewelers Row
Hotel in Chicago Loop, ChicagoFree cancellation options available8.1Scored 8.1Very goodRated very good· 339 reviewsSonder Jewelers Row features accommodation within 700 metres of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, a microwave and a toaster.
Location was good, property was clean and as pictured
The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
Hotel in Lakeview, ChicagoFree cancellation options available8.3Scored 8.3Very goodRated very good· 256 reviewsIn the Lakeview district of Chicago, close to Wrigley Field, The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit has free WiFi and a washing machine.
Around the corner from Wrigley. Clean. Safe. Awesome!
Sonder South Wabash
Hotel in South Loop, ChicagoFree cancellation options available8.5Scored 8.5Very goodRated very good· 501 reviewsIn the South Loop district of Chicago, close to Field Museum of Natural History, Sonder South Wabash has free WiFi and a washing machine.
Location, everything works well within the apartment
Sonder Greektown
Hotel in West Loop, ChicagoFree cancellation options available8.2Scored 8.2Very goodRated very good· 124 reviewsIn the West Loop district of Chicago, close to Union Station, Sonder Greektown has free WiFi and a washing machine.
Space including storage. Quiet apart from a/c unit.
Sonder The Burnham
Hotel in West Loop, ChicagoFree cancellation options available8.4Scored 8.4Very goodRated very good· 70 reviewsSonder The Burnham offers accommodation within 1.6 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.
Good location, clean and nice fully equipped kitchen.
Sonder Market Hall
Hotel in West Loop, ChicagoFree cancellation options available8.4Scored 8.4Very goodRated very good· 91 reviewsLocated within 1.2 km of United Center and 2.8 km of Union Station, Sonder Market Hall provides rooms with air conditioning and a private bathroom in Chicago.
Easy entrance, great location, clean and beautiful.
ONE ROOM in AN APT HAVEN
Hotel in ChicagoFree cancellation options available5.5Scored 5.5AverageRated passable· 2 reviewsSituated in Chicago, 10 km from United Center and 11 km from Lincoln Park Zoo, ONE ROOM in AN APT HAVEN offers a garden and air conditioning.
Casa Cerca De La Playa
Hotel in Chicago8.0+ review score8.5Scored 8.5Very goodRated very good· 17 reviewsSet in Chicago, 6.9 km from Museum of Science and Industry - Chicago and 14 km from Guaranteed Rate Field, Casa Cerca De La Playa offers a garden and air conditioning.
Friendly. Told me what he expected and was a nice person.
The Twin Lions: Bespoke Travel Lodge w/ Speakeasy*
Hotel in Chicago8.0+ review score9.8Scored 9.8ExceptionalRated exceptional· 10 reviewsThe Twin Lions: Bespoke Travel Lodge w/ Speakeasy* is a recently renovated apartment in Chicago, where guests can make the most of its garden and bar.
Well located, VERY CLEAN, unique decor, stocked kitchen.
Chicago Charm
Hotel in Chicago8.0+ review score9.7Scored 9.7ExceptionalRated exceptional· 35 reviewsOffering garden views, Chicago Charm is an accommodation set in Chicago, 11 km from Lincoln Park Zoo and 13 km from 360 Chicago.
I liked that we had private parking and plenty of room.
Romantic 3 Bed Home In The Heart Of The Park
Hotel in Chicago8.0+ review score9.1Scored 9.1SuperbRated superb· 16 reviewsSituated 6.2 km from Guaranteed Rate Field, 11 km from Art Institute of Chicago and 11 km from Field Museum of Natural History, Romantic 3 Bed Home In The Heart Of The Park features accommodation...
City Villa Sleeps 10-20 Free TV & Parking
Hotel in Lakeview, Chicago8.0+ review score9.4Scored 9.4SuperbRated superb· 9 reviewsSet in Chicago, City Villa Sleeps 10-20 Free TV & Parking is a recently renovated accommodation, 2.5 km from North Avenue Beach and 1.9 km from Wrigley Field.
Beliggenhet var helt fint. Greit å reise dit vi skulle både med buss og bane.
9.6Scored 9.6ExceptionalRated exceptional· 11 reviewsBoasting accommodation with a patio, Winter Wonderland Retreat and Your Chicago Chill Getaway is set in Chicago.
広い。綺麗。洗濯機と洗剤が準備されている。都心部には行きやすく周りは静か。オーナーとは結局一度も話さなかったが十分にコミュニケーションがとれた。タオルはある。
9.4Scored 9.4SuperbRated superb· 7 reviewsLocated in Chicago in the Illinois region, Spacious Row Home next Transit near Downtown w Parking features a patio.
Everything was clean and comfortable for 5 adults and 11 kids
Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
Hotel in Chicago8.0+ review score9.8Scored 9.8ExceptionalRated exceptional· 22 reviewsNorthside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find is a recently renovated holiday home in Chicago, where guests can make the most of its garden and tennis court.
The place is in a very cute neighborhood and was super clean.
FAQs about hotels in Chicago
Holiday rentals that guests love in Chicago
- 8.6Scored 8.6FabulousRated fabulous· 906 reviewsThe location was excellent for our travel plans. We were there to hear music at Buddy Guy's Legends and do some sight seeing during the day. The stadium tour of Wriggley Field was a high light. The Italian Village was a nice surprise with fantastic food. My partner is gluten free and the options they had were outstanding. The restaurant is a bit pricey.
EJAYBICKUnited States - From £274.43 per night9.0Scored 9.0SuperbRated superb· 61 reviewsRosa & Edith were attentive to our needs and expectations. The entire staff was friendly, accommodating and engaging. The Villa was at our disposal, and we were able to enjoy the amenities with our daughter and her husband who live nearby.NosalUnited States
- 10Scored 10ExceptionalRated exceptional· 1 reviewOne of the nicest vacation rental apartments I have stayed in. Very well appointed, kitchen had everything you could need including a full size washer and dryer. Having the back balcony was great.MargueriteCanada
- From £144.60 per night8.4Scored 8.4Very goodRated very good· 91 reviewsLooks like a vacation houseLLinhUnited States
- 9.3Scored 9.3SuperbRated superb· 43 reviewsUpdated, well maintained. Nearby is a cozy little Italian village with restaurants and outdoor seating that was great! Overall it was beautiful, cozy and comfortable.DawnUnited States
- From £274.43 per night9.0Scored 9.0SuperbRated superb· 61 reviewsThe Villa is lovely and the host was great. They have great options for breakfast which you prepare yourself. Location was really nice - lovely the neighborhood. Loved the wine on tap!
SydneyMexico - 8.6Scored 8.6FabulousRated fabulous· 906 reviewsBreakfast was convenient. Location can't be beaten. Rooms are unexpectedly roomy. The staff was extremely friendly and helpful. We enjoyed the Grillroom Chophouse (reasonable prices) across the street and the Italian Village (whimsical interior) down the block -- both recommended.
WilsonUnited States - From £217.75 per night8.7Scored 8.7FabulousRated fabulous· 359 reviewsThe location was convenient to restaurants, and most importantly, to our family members in Ukrainian Village. The staff was friendly and helpful. Our room was very comfortable, very functional, and had an excellent shower.
JoanneUnited States - 7.2Scored 7.2GoodRated good· 888 reviewsLocation, close to the Loop and in the middle of the Hellenic villageJosuePuerto Rico
- 9.8Scored 9.8ExceptionalRated exceptional· 30 reviewsMagnolia Studios exceeded my expectations. The location was superb, and was perfect for a few days in town. Parking was never a problem. The studio itself was clean, comfortable, and quiet. Kitchen was adequately stocked with everything you may need for cooking a simple meal, and making a fresh cup of coffee with the Kuerig. As long as you read all instructions it's very simple to find the entrance. As an owner of my own vacation rental I would highly recommend Magnolia Studios.
AmyUnited States
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