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Vacation Rentals in Chicago
Find the vacation rentals that appeal to you the most
Vacation Rentals for every style
Find the right vacation rental for you in Chicago
The best vacation rentals in Chicago
Check out our selection of great vacation rentals in Chicago
Filter by:
2F Chicago's Little Italy near West Loop & Downtown
Chicago
2F Chicago's Little Italy near West Loop & Downtown offers accommodations in Chicago, 1.9 miles from Union Station and 2 miles from Willis Tower.
D
Debbie
From
United KingdomOutstanding accommodation. Fabulously comfortable beds. Great shared area. Super bathrooms. Incredibly stocked with bedding, toiletries, kitchen equipment etc. Very clean. Great location near lovely restaurants and L stations to get you into the city. Highly recommended for a trip to Chicago. Great communication from owners.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 195 reviews
Price from
NZD 309.20
1 night, 2 adults
The Avondale Guesthouse
Chicago
The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.
K
Kam
From
United StatesEasy access to a nice property in a good location. The hosts were amazing and easy to communicate with. Noemi was so nice and decorated the house for the holiday- it was so cool! We had a blast!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 128 reviews
Price from
NZD 409.19
1 night, 2 adults
Ray's Bucktown Bed and Breakfast
Logan Square, Chicago
Ray's Bucktown Bed and Breakfast provides a sauna and free private parking, and is within 3.1 miles of Lincoln Park Zoo and 3.2 miles of Wrigley Field.
M
Marcus
From
CanadaLike going back to the university hostel of long forgotten days. People could be staying there for a night, but it looks like they stayed there longer.
The kitchen is always open, so it is a big plus for hungry and thirsty travelers. Anyone can just grab something there and make yourself at home like you did in your own kitchen, excellent.
The location is a real plus and sunset walk nearby give you a good feel of American lives seeing couples young and old taking their dogs for a walk. Somewhat, the building around reminds me of Boston or Montreal.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 172 reviews
Price from
NZD 290.84
1 night, 2 adults
Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub
Chicago
A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.
A
Ashley
From
United StatesThis is truly a home away from home. We felt at ease the entire stay and even though we had a jam-packed trip, coming back to the house felt like coming home. The neighborhood is great for walking, and feels extremely safe. There are fantastic coffee shops and restaurants all throughout the neighborhood, and the street parking is plentiful, which makes staying in the city so much easier. I had exactly 30 minutes to myself during the trip, and while everyone else rested, I got in the hot tub and really recharged for the rest of our evening. It was cool outside and perfect in the tub. I cannot more highly recommend this home, and I can't thank Andrea enough. The house is historic and beautiful, and very clean. The beds are so comfortable, and having more than one bathroom is such a bonus. We ended up needing to use the dryer, and it's so nice to have laundry facilities when you accidentally end up with a wet shoe and socks! There's a fireplace and seating for hanging out inside when it's chilly, and it's super cozy. There's a Keurig for coffee and Andrea even offered to get us milk for coffee, but we opted to walk down to the local spots and soak in the neighborhood. I've said a lot but I still feel like I'm not capturing how great the property really is. If you've found this one, stop scrolling!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 8 reviews
Price from
NZD 515.33
1 night, 2 adults
1F Cozy Home in Little Italy near Downtown West Loop United Center
Chicago
1F Cozy Home in Little Italy near Downtown West Loop United Center is located in Chicago, just 1.1 miles from United Center and 2.4 miles from Willis Tower.
J
Jen
From
United StatesBeautiful historic home just a short train ride from downtown. The apartment is equipped with everything you could ever want or need and then some. It is so comfortable and cozy and very affordable. This is the best vacation rental we’ve stayed in. Thank you, John, for the great hospitality.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 88 reviews
Price from
NZD 347.85
1 night, 2 adults
Designer Themed 4 Bedroom in Best Location with Patio and Fireplace
Near North Side, Chicago
Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.
S
Strand
From
United StatesThis was our first attempt at a non-hotel location. I was surprised how much we appreciated the home's amenities away from home. Amenities like; multiple bathrooms, full kitchen, private off-street parking and a pleasant neighborhood.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 30 reviews
Price from
NZD 719.75
1 night, 2 adults
4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome
Near North Side, Chicago
A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
NZD 857.17
1 night, 2 adults
The Polo Inn Bridgeport U.S.A.
Bridgeport, Chicago
Offering air-conditioned rooms in the Bridgeport district of Chicago, The Polo Inn Bridgeport U.S.A. Is 1.1 miles from Guaranteed Rate Field.
G
Greg
From
New ZealandGreat personal service and cooked-to-order breakfast by the wonderful proprietors; very spacious and comfortable rooms (I has a two room suite). Although the McCormick Place Convention Centre where I was attending a conference is 4 miles away, they happily dropped me to the door each morning. Amazing - thanks!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 49 reviews
Price from
NZD 489.56
1 night, 2 adults
Villa D' Citta
Lincoln Park, Chicago
Villa D' Citta enjoys a location in Chicago, 1.4 miles from North Avenue Beach and a 18-minute walk from Lincoln Park Zoo.
M
Marcia M
From
United StatesI loved the kitchen, the room, the courtyard, everything about it! Best B&B ever!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 33 reviews
Price from
NZD 353.60
1 night, 2 adults
Sentral Michigan Avenue
Hotel in Chicago Loop, Chicago
Sentral Michigan Avenue has a fitness center, garden, a shared lounge and restaurant in Chicago. This 3-star hotel offers a shared kitchen, a 24-hour front desk and free WiFi.
D
Diana
From
MexicoSentral has a great location, a lot of bus stops around, two CTA stations within 10 min walks and metra station 5 min away, which worked great for us since we were going to de McCormick center which also has a metra station.
The flat is beautifully furnished, the bed and pillows were great, the kitchen is well equipped and you are providded with cleaning soap for dishes and clothes, as well as shower gel, shampoo, conditioner and lotion.
The gym is great too, well equipped, we didn't go into the pool because we didn't bring any swuimsuits but ir was beautyful, indoor and had a great view.
I would definety saty here again in my next visit to Chicago
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,019 reviews
Price from
NZD 290.30
1 night, 2 adults
Most booked vacation rentals in Chicago and surrounding area in the past month
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 172 reviews
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 208 reviews
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 195 reviews
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 333 reviews
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 391 reviews
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 331 reviews
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 322 reviews
Popular with guests booking vacation rentals in Chicago
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 63 reviews
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,019 reviews
Enjoy breakfast in Chicago and nearby
Loop 1BR w Lounge Rooftop nr Art Institute CHI-103 offers accommodations in Chicago, a 1-minute walk from Chicago Symphony Orchestra and half a mile from Willis Tower.
Loop Studio w Gym Pool nr Chicago Riverwalk CHI-240 is located in Chicago, just a 9-minute walk from Chicago Symphony Orchestra and half a mile from Shops at Northbridge.
Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop
Chicago Loop, Chicago
Breakfast options
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 64 reviews
Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster,...
Loop 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382 offers accommodations in Chicago, a 11-minute walk from Cloud Gate – The Bean and half a mile from Chicago Symphony Orchestra.
Loop 1BR w Pool Gym nr Financial District CHI-282 is located in Chicago, just a 15-minute walk from Millennium Park and 0.9 miles from DePaul University.
Loop 1BR w Pool Gym nr the L Riverwalk CHI-242
Chicago Loop, Chicago
Breakfast options
Loop 1BR w Pool Gym nr the L Riverwalk CHI-242 features accommodations in the center of Chicago, 1.5 miles from Ohio Street Beach and a 11-minute walk from Willis Tower.
Just a 15-minute walk from Millennium Park and 0.9 miles from DePaul University, Loop 1BR w Gym Pool WD nr Financial District CHI-222 features accommodations in Chicago with a shared lounge.
The Penthouse at Grand Plaza
River North, Chicago
Breakfast options
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 102 reviews
Located in the heart of downtown Chicago, just 3 blocks away from the Magnificent Mile, this self-catering apartment features a balcony with iconic views of the city. Free WiFi access is available.
Vacation Rentals with swimming pools in Chicago and nearby
Streeterville 2BR w Deck Gym nr Beach Park CHI-589 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago.
Level Chicago River North
River North, Chicago
Swimming pool
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 3 reviews
Located in Chicago and with Oak Street Beach reachable within 1.5 miles, Level Chicago River North provides a seasonal outdoor swimming pool, non-smoking rooms, free WiFi throughout the property and a...
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 52 reviews
Just a 2-minute walk from Water Tower Chicago and 500 yards from 360 Chicago, The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile features accommodations in Chicago, with a fitness center...
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 7 reviews
A 3-minute walk from Union Station in the center of Chicago, Jeffjack Heated Pool Penthouse in Chicago's West Loop provides accommodations with access to a hot tub, fitness room, and indoor pool.
S Loop 1BR w Pool Gym nr Soldier Field CHI-350 features accommodations in the center of Chicago, a 8-minute walk from Field Museum of Natural History and 0.7 miles from Grant Park.
S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740 offers accommodations in the center of Chicago, a 8-minute walk from Field Museum of Natural History and 0.7 miles from Grant Park.
A 8-minute walk from Field Museum of Natural History in the center of Chicago, S Loop 1BR w pool gym spa nr Grant Park CHI-744 offers accommodations with access to an indoor pool.
A 8-minute walk from Field Museum of Natural History in the center of Chicago, S Loop 1BR w Pool Gym Spa nr Grant Park CHI-741 features accommodations with access to an indoor pool.
These vacation rentals in Chicago and nearby have options with free cancellation
Hyde Park Modern Private Room - Near Univ of Chicago
Chicago
Free cancellation options available
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 31 reviews
Hyde Park Modern Private Room - Near Univ of Chicago is located in Chicago, just 1.5 miles from Oakwood Beach and 2.3 miles from Museum of Science and Industry - Chicago.
From NZD 223.64 per night
5430 Happy Home
Chicago
Free cancellation options available
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 391 reviews
5430 Happy Home enjoys a location in Chicago, 2.8 miles from Museum of Science and Industry - Chicago and 3 miles from Guaranteed Rate Field. This homestay offers a shared kitchen and free Wifi.
From NZD 147.12 per night
Streeterville Studio w Gym Pool nr Navy Pier CHI-445
Streeterville, Chicago
Free cancellation options available
Streeterville Studio w Gym Pool nr Navy Pier CHI-445 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago.
Streeterville 1BR w Gym Pool nr Navy Pier CHI-412
Streeterville, Chicago
Free cancellation options available
Streeterville 1BR w Gym Pool nr Navy Pier CHI-412 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago. This apartment offers an elevator and free Wifi.
Kasa South Loop Chicago
South Loop, Chicago
Free cancellation options available
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 331 reviews
Kasa South Loop Chicago enjoys a location in Chicago, a 16-minute walk from Grant Park and one mile from Art Institute of Chicago.
River North 1br w gym lounge roof nr L CHI-838
River North, Chicago
Free cancellation options available
River North 1br w gym lounge roof nr L CHI-838 offers accommodations in Chicago, a 7-minute walk from Shops at Northbridge and one mile from Millennium Station.
River N 2BR w Gym WD nr Magnificent Mile CHI-164
River North, Chicago
Free cancellation options available
River N 2BR w Gym WD nr Magnificent Mile CHI-164 offers accommodations in Chicago, a 6-minute walk from Shops at Northbridge and one mile from Millennium Station.
River N 2BR w Gym WD nr Magnificent Mile CHI-160
River North, Chicago
Free cancellation options available
River N 2BR w Gym WD nr Magnificent Mile CHI-160 offers accommodations in Chicago, a 6-minute walk from Shops at Northbridge and one mile from Millennium Station.
Highly rated vacation rentals in Chicago and nearby
Perfect place to enjoy the city or just relax
Chicago
8.0+ review score
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 161 reviews
Perfect place to enjoy the city or just relax offers accommodations in Chicago, 2.7 miles from United Center and 4.4 miles from Union Station.
Forrestville Ave Large Suite
Bronzeville, Chicago
8.0+ review score
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 109 reviews
Forrestville Ave Large Suite is located in Chicago, just 2.8 miles from Museum of Science and Industry - Chicago and 4.5 miles from Field Museum of Natural History.
Aurelien Spacious Apartments in the Heart of Gold Coast
Chicago
8.0+ review score
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 56 reviews
Aurelien Spacious Apartments in the Heart of Gold Coast provides accommodations within 0.7 miles of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster, and a fridge.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 20 reviews
Just a 19-minute walk from Union Station and 1.2 miles from Willis Tower, K2 Sky High Apartments with Stunning Chicago Views in West Loop features accommodations in Chicago, with a shared lounge.
Historic luxury Townhouse in Downtown Chicago
Chicago
8.0+ review score
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 9 reviews
Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 16-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.
Studio flat in the heart of Downtown Chicago
Chicago
8.0+ review score
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 24 reviews
Studio flat in the heart of Downtown Chicago offers accommodations in Chicago, a 16-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 5 reviews
Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests features accommodations in Chicago with a garden.
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 26 reviews
Just a 15-minute walk from Union Station and 1.1 miles from Willis Tower, Sage Modern Apartments Near Union Park in West Loop features accommodations in Chicago, with a fitness center.
FAQ about vacation rentals in Chicago
Vacation Rentals That Guests Love in Chicago
Avg. price/night: NZD 216.44
Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 220 reviews
Im so happy i came across Villa Dubois Guesthouse. The whole property is clean and organized, free street parking, neighborhood is quiet. I love the full functional kitchen where you can prepare meals.security cameras around the common area for safety.If you dont mind sharing a space with strangers,this a nice budget friendly place to stay😊
Guest review by
LIW-LIWAYoung couple
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 35 reviews
It's like a little courtyard villa in Montparnasse, with a wrought-iron balcony and birds singing in the garden. Great shower!
Guest review by
MarySolo traveler
Avg. price/night: NZD 950.96
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 33 reviews
Rosa & 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.
Guest review by
NosalYoung couple
Avg. price/night: NZD 950.96
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 33 reviews
The 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!
Guest review by
SydneyGroup
