Skip to main content
Manage my booking

Vacation Rentals in Chicago

Find the vacation rentals that appeal to you the most

December 2025

123456
78910111213
14151617181920
21222324252627
28293031

January 2026

123
45678910
11121314151617
18192021222324
25262728293031
Check-in date - Check-out date

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:

Review score

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.

E
Eduardo
From
Puerto Rico
Space, accomodations, and location
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 195 reviews
Price from
AR$ 258,974.80
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 States
Easy 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
AR$ 342,724.37
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.

C
Carlos
From
Spain
Lots of personality. Everyone working there has a great attitude. Happy people who make you feel happy! Breakfast is amazing
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 172 reviews
Price from
AR$ 243,594.57
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 States
This 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
AR$ 431,624.66
1 night, 2 adults

Lincoln Park 3 BR Penthouse

Lincoln Park, Chicago

Lincoln Park 3 BR Penthouse is located in Chicago, just 1.6 miles from Fullerton Beach and 1.3 miles from Wrigley Field.

M
Maria Jose
From
Ecuador
An amazing experience. The place is beautiful and it was really easy to communicate with the host. Cleanliness was wonderful and I felt right at home. I would definitely consider coming back.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 64 reviews
Price from
AR$ 258,974.80
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.

T
Todd
From
Canada
3 bedroom and all the amemities.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 88 reviews
Price from
AR$ 291,346.65
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 States
This 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
AR$ 602,835.78
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
AR$ 717,935.69
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
Garcia
From
United States
Great location in Bridgeport; excellent breakfast and hospitality! A true old school bed and breakfast.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 49 reviews
Price from
AR$ 410,043.43
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 States
I 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
AR$ 296,166.46
1 night, 2 adults
All vacation rentals in Chicago

Most booked vacation rentals in Chicago and surrounding area in the past month

See all

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 172 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 8.9
Excellent - What previous guests thought, 208 reviews

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 332 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 9.3
Wonderful - What previous guests thought, 321 reviews

Popular with guests booking vacation rentals in Chicago

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 64 reviews

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,016 reviews

These vacation rentals in Chicago and nearby have options with free cancellation

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 AR$ 187,313.10 per night

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.

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 2BR w Pool Gym nr Financial District L CHI-247 features accommodations in the center of Chicago, 1.5 miles from Ohio Street Beach and a 11-minute walk from Willis Tower.

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.

Enjoy breakfast in Chicago and nearby

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.

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.

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 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.

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 332 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 offers accommodations in Chicago, a 7-minute walk from Shops at Northbridge and one mile from Millennium Station.

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...

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.

Vacation Rentals with swimming pools in Chicago and nearby

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 53 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.

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.

Highly rated vacation rentals in Chicago and nearby

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.

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.

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.

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 25 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.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 19 reviews

Avenir West Loop Penthouses with Iconic City Views features a garden and accommodations with a kitchen in Chicago, 1.6 miles from Water Tower Chicago.

Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 6 reviews

Chic & Central 420-Friendly 3BR Oasis with Optional Parking Near UIC, Roosevelt Station & Chicago's Top Attractions offers accommodations in Chicago, 1.5 miles from Field Museum of Natural History and...

FAQ about vacation rentals in Chicago

Vacation Rentals That Guests Love in Chicago

See all
Avg. price/night: AR$ 178,404.86
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-LIWA
Young 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
Mary
Solo traveler
Avg. price/night: AR$ 796,495.01
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
Nosal
Young couple
Avg. price/night: AR$ 796,495.01
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
Sydney
Group
gogless