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The best vacation rentals in Chicago

Check out our selection of great vacation rentals in Chicago

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Review score

The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.

Accommodating host. Had everything we needed. Glad we stayed here and would do it again.
Review score
Wonderful
138 reviews
Price from
MXN 5,227.20
1 night, 2 adults

The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 0.7 mi away. Parking is free with permit provided by The Sono Chicago.

Great location, walk to Second City . Chocolate croissants
Review score
Exceptional
332 reviews
Price from
MXN 3,902.98
1 night, 2 adults

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.

The room was cozy and clean. The location was nice and the breakfast was amazing.
Review score
Wonderful
221 reviews
Price from
MXN 4,088.64
1 night, 2 adults

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.

Review score
Exceptional
5 reviews
Price from
MXN 9,660.64
1 night, 2 adults

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.

Super friendly hosts met me and walked me through. The newly renovated brownstone basement apartment was comfy and clean!
Review score
Wonderful
96 reviews
Price from
MXN 2,178
1 night, 2 adults

Villa D' Citta enjoys a location in Chicago, 1.4 miles from North Avenue Beach and a 18-minute walk from Lincoln Park Zoo.

This place was stunning! The location is great, the building is beautiful, the owners were so kind and the food was delicious. We had zero complaints and will most definitely be back again.
Review score
Wonderful
44 reviews
Price from
MXN 3,985.26
1 night, 2 adults

Just Minutes from Downtown Chicago is located in Chicago, just 1.4 miles from Oakwood Beach and 2.3 miles from Guaranteed Rate Field.

The hospitality of the host and the comfort of the room. Very quiet environment.
Review score
Wonderful
7 reviews
Price from
MXN 42,592
1 night, 2 adults

1.9 miles from Wrigley Field in Chicago, Roscoe Village Guesthouse features accommodations with access to a fitness room.

It’s great location and bigger than expected with two large bathrooms. It’s in a very walkable area and close to public transportation. We were there to visit DePaul and Loyola and it’s was super convenient. I would definitely stay again! The communication and support was also great!
Review score
Wonderful
40 reviews
Price from
MXN 4,336.64
1 night, 2 adults

A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.

Everything was fantastic!
Review score
Wonderful
7 reviews
Price from
MXN 7,744
1 night, 2 adults

Lincoln Park Gem is located in Chicago, just 1.6 miles from Fullerton Beach and 1.3 miles from Wrigley Field. This apartment offers air-conditioned accommodations with a patio.

Good location!
Review score
Wonderful
71 reviews
Price from
MXN 3,833.28
1 night, 2 adults
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Enjoy breakfast in Chicago!

  • Review score
    Wonderful · 44 reviews

    Villa D' Citta enjoys a location in Chicago, 1.4 miles from North Avenue Beach and a 18-minute walk from Lincoln Park Zoo.

    Guest review
    Very beautiful and comfortable place, but definitely go there again
    From MXN 7,494.36 per night
  • Review score
    Excellent · 49 reviews

    Wicker Park Inn enjoys a location in Chicago, 2.3 miles from United Center and 2.8 miles from Water Tower Chicago.

    Guest review
    Excellent location, comfortable space, friendly staff.
    From MXN 6,948.99 per night
  • Review score
    Excellent · 66 reviews

    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.

    Guest review
    EVERYONE WAS SO NICE OH MY GOD IT DOESNT GET BETTER
    From MXN 5,901.51 per night
  • Review score
    Wonderful · 189 reviews

    Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena provides beachfront accommodations in Chicago.

    Guest review
    I love the casual place to stay and easy to access many locations around.
  • Review score
    Wonderful · 138 reviews

    The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.

    Guest review
    Responsive, accommodating hosts. Great location, comfortable stay
    From MXN 9,188.26 per night
  • Breakfast options
    Review score
    Exceptional · 332 reviews

    The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 0.7 mi away. Parking is free with permit provided by The Sono Chicago.

  • Review score
    Wonderful · 221 reviews

    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.

    Guest review
    The room was cozy and clean. The location was nice and the breakfast was amazing.
    From MXN 5,534.09 per night
  • Review score
    Wonderful · 100 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.

    Guest review
    The condo was very clean and very well-stocked. It was a home away from home. Also; the location was perfect.

These vacation rentals in Chicago have options with FREE cancellation

  • Review score
    Wonderful · 7 reviews

    Just Minutes from Downtown Chicago is located in Chicago, just 1.4 miles from Oakwood Beach and 2.3 miles from Guaranteed Rate Field.

    From MXN 42,592 per night
  • Free cancellation options available
    Review score
    Excellent · 1,850 reviews

    Sentral Michigan Avenue offers accommodations within 1.1 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    From MXN 12,817.86 per night
  • Review score
    Very Good · 245 reviews

    Sonder by Marriott Bonvoy The Burnham Apartments Loop offers accommodations within one mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    Guest review
    Upon entrance, it was a great look. Nicely decorated. Very clean.
  • Review score
    Very Good · 216 reviews

    Sonder by Marriott Bonvoy Market Hall Apartments West Loop offers accommodations in Chicago, a 13-minute walk from United Center and 1.7 miles from Union Station.

    Guest review
    Easy instructions, easy access, a lot of things to do around, save neighborhood. I loved it.
    From MXN 5,776.48 per night
  • Review score
    Excellent · 274 reviews

    Sonder by Marriott Bonvoy The Opal Apartments River North features accommodations within 0.4 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

  • Review score
    Very Good · 299 reviews

    The Double Play - 1 Min Walk to Wrigley! Spacious 2BR - Perfect for Cubs Fans! offers accommodations in Chicago, a 3-minute walk from Wrigley Field and 2.4 miles from Lincoln Park Zoo.

    Guest review
    Came for baseball games,it was a perfect location.
    From MXN 8,154.76 per night
  • Free cancellation options available
    Review score
    Very Good · 358 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.

    Guest review
    Pretty good stay. Dee was super nice and accommodating.
    From MXN 3,461.49 per night
  • Review score
    Very Good · 541 reviews

    Sonder by Marriott Bonvoy South Wabash Apartments South Loop offers accommodations in Chicago, 1.2 miles from Art Institute of Chicago and 1.2 miles from Chicago Symphony Orchestra.

Highly-rated vacation rentals in Chicago

  • Review score
    Exceptional · 72 reviews

    1F Cozy Home in Little Italy near Downtown West Loop United Center offers accommodations in Chicago, 2.4 miles from Willis Tower and 2.4 miles from Union Station.

    Guest review
    Spacious and cleanly, also has a home like feel to it.
  • Review score
    Wonderful · 96 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.

    Guest review
    It’s very clean and spacious, I really recommend it.
  • Review score
    Wonderful · 40 reviews

    1.9 miles from Wrigley Field in Chicago, Roscoe Village Guesthouse features accommodations with access to a fitness room.

    Guest review
    The property manager, Stephanie, was excellent and easy to work with.
    From MXN 18,415.47 per night
  • Review score
    Very Good · 28 reviews

    Cozy & Modern 3BR Apartment - Division 201W 301W REP offers accommodations in Chicago, 3.3 miles from Union Station and 3.4 miles from 360 Chicago.

    Guest review
    Great service, clean, beds are comfortable 👌 I recommend it 100%
    From MXN 7,863.12 per night
  • Review score
    Very Good · 46 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.

    Guest review
    Andy’s place has everything you need for a very comfortable stay, the place is super clean and he was always available for any questions we had.
    From MXN 2,687.30 per night
  • Review score
    Very Good · 51 reviews

    ✪ Cozy 1 Bedroom close to Downtown Chicago ✪ offers accommodations in Chicago, 2.8 miles from Chicago Museum of Contemporary Art and 3 miles from Shops at Northbridge.

    Guest review
    The closeness to public transport and cute neighborhood.
  • Review score
    Excellent · 26 reviews

    Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.

    Guest review
    The Location was nice, worked really well for us to be able to prepare meals and cook when we wanted to, nice space to sit and chat. Having where to park the car was a plus.
  • Review score
    Very Good · 13 reviews

    Wrigleyville Friends Unit - 5bdrm is located in Chicago, just 1.7 miles from Fullerton Beach and a 8-minute walk from Wrigley Field.

    Guest review
    No breakfast. Location was good for us it’s an easy balk to Wrigley field.
    From MXN 19,360 per night

FAQ about vacation rentals in Chicago

Vacation Rentals That Guests Love in Chicago

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  • Review score
    Good · 14 reviews
    What a great location and stunning apartment! The apartment was extremely close to shops and restaurants and about an 8 min walk to the train and wriggly field. Communication with MJ was fantastic. It was beautifully decorated and just about the cleanest vacation rental I’ve ever stayed in.
    Guest review by
    Jon
    Family with young children
  • Avg. price/night: MXN 4,485.15
    Review score
    Fair · 212 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
  • Review score
    Exceptional · 33 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
  • Review score
    Very Good · 937 reviews
    The 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.
    Guest review by
    EJAYBICK
    Young couple
  • Avg. price/night: MXN 7,494.36
    Review score
    Wonderful · 44 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
  • Review score
    Wonderful · 4 reviews
    One 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.
    Guest review by
    Marguerite
    Solo traveler
  • Avg. price/night: MXN 5,776.48
    Review score
    Very Good · 216 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple
  • Review score
    Exceptional · 42 reviews
    Updated, well maintained. Nearby is a cozy little Italian village with restaurants and outdoor seating that was great! Overall it was beautiful, cozy and comfortable.
    Guest review by
    Dawn
    Travelers with friends
  • Avg. price/night: MXN 7,494.36
    Review score
    Wonderful · 44 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
  • Review score
    Very Good · 937 reviews
    Breakfast 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.
    Guest review by
    Wilson
    Young couple