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Vacation apartments in Chicago

Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Apartment
    • House
    • Bed and breakfast

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Bedrooms

    • Any
    • 1 bedroom
    • 2+ bedrooms

  • Booking Options

    • Instant Booking

  • Services

    • WiFi
    • Pool
    • Kitchen
    • TV
    • Air conditioning
    • Parking
    • Washing machine
    • Balcony/patio
    • Microwave
    • Dishwasher
    • Fireplace
    • Jacuzzi
    • Yard
    • Crib
    • Sauna
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Vacation apartments in Chicago: Recommended vacation rentals

Vacation apartments in Chicago: find your perfect rental from just $102 per night!

Apartment Tri-Taylor
Jan 4 - Jan 11
Free cancellation
Apartment ∙ 3 guests ∙ 2 bedrooms

102 m² Apartment

Tri-Taylor, Chicago, Illinois, United States
$334
per night
Outstanding(10 ratings)
$334
per night
View deal
Apartment Roscoe Village
-51%
Jan 31 - Feb 7
Free cancellation
Apartment ∙ 10 guests ∙ 1 bedroom

241 m² Apartment

Roscoe Village, Chicago, Illinois, United States
$448$494
per night
Very good
$448$494
per night
View deal
Apartment Cicero
Jun 14 - Jun 21
Free cancellation
Apartment ∙ 5 guests ∙ 2 bedrooms

1000 m² Apartment

Cicero, Cicero Township, Illinois, United States
$341
per night
$341
per night
View deal
Apartment Tri-Taylor
-63%
Jan 19 - Jan 26
Free cancellation
Apartment ∙ 4 guests ∙ 2 bedrooms

111 m² Apartment

Tri-Taylor, Chicago, Illinois, United States
$518$206
per night
$518$206
per night
View deal
Apartment Heart of Chicago
Jul 5 - Jul 12
Free cancellation
Apartment ∙ 6 guests ∙ 2 bedrooms

121 m² Apartment

Heart of Chicago, Chicago, Illinois, United States
$583
per night
$583
per night
View deal
Apartment West Garfield Park
Jun 14 - Jun 21
Free cancellation
Apartment ∙ 4 guests ∙ 2 bedrooms

186 m² Apartment

West Garfield Park, Chicago, Illinois, United States
$396
per night
$396
per night
View deal
Apartment West Town
-67%
Apr 13 - Apr 20
Free cancellation
Apartment ∙ 4 guests ∙ 1 bedroom

69 m² Apartment

West Town, Chicago, Illinois, United States
$582$194
per night
Outstanding(3 ratings)
$582$194
per night
View deal
Apartment Grand Boulevard
-28%
Jan 18 - Jan 25
Apartment ∙ 6 guests ∙ 2 bedrooms

111 m² Apartment

Grand Boulevard, Chicago, Illinois, United States
$309$226
per night
(2 ratings)
$309$226
per night
View deal
Apartment Near West Side
-48%
Jan 18 - Jan 25
Apartment ∙ 10 guests ∙ 3 bedrooms

171 m² Apartment

Near West Side, Chicago, Illinois, United States
$836$442
per night
Outstanding(4 ratings)
$836$442
per night
View deal
Apartment South Austin
Jan 3 - Jan 10
Free cancellation
Apartment ∙ 12 guests ∙ 4 bedrooms

185 m² Apartment

South Austin, Chicago, Illinois, United States
$466
per night
Excellent(3 ratings)
$466
per night
View deal
Apartment Rogers Park
-64%
Jan 25 - Feb 1
Apartment ∙ 6 guests ∙ 2 bedrooms

83 m² Apartment

Rogers Park, Chicago, Illinois, United States
$554$199
per night
Excellent(4 ratings)
$554$199
per night
View deal
Apartment South Austin
-34%
Apr 5 - Apr 12
Free cancellation
Apartment ∙ 8 guests ∙ 3 bedrooms

102 m² Apartment

South Austin, Chicago, Illinois, United States
$580$393
per night
Outstanding(1 rating)
$580$393
per night
View deal
Apartment South Austin
-37%
Jan 18 - Jan 25
Apartment ∙ 10 guests ∙ 2 bedrooms

139 m² Apartment

South Austin, Chicago, Illinois, United States
$617$391
per night
Outstanding(2 ratings)
$617$391
per night
View deal
Apartment McKinley Park
-54%
Jan 18 - Jan 25
Apartment ∙ 2 guests ∙ 1 bedroom

55 m² Apartment

McKinley Park, Chicago, Illinois, United States
$492$227
per night
$492$227
per night
View deal
Apartment Heart of Chicago
-7%
Jan 25 - Feb 1
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment

Heart of Chicago, Chicago, Illinois, United States
$169$142
per night
$169$142
per night
View deal
Show all 3,866 properties

Popular Amenities for Vacation apartments in Chicago

Find the perfect home for your stay

Apartments with internet

Apartments with pools

Apartments with kitchen

Apartments with TV

Top-Rated apartments in Chicago

Browse our top rated apartments offers

Condo Near West Side
Jan 19 - Jan 26
-86%
$804
$116 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding(4 ratings)
Near West Side, Chicago, Illinois, United States
Free cancellation
View deal
Apartment Grand Boulevard
Feb 1 - Feb 8
-35%
$533
$336 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent(3 ratings)
Grand Boulevard, Chicago, Illinois, United States
Free cancellation
View deal
Apartment Near West Side
Jan 4 - Jan 11
-65%
$588
$270 per night
Apartment ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Near West Side, Chicago, Illinois, United States
View deal

Best Deals and Discounts on Apartments

Save up to 74%

Apartment South Loop
Jan 18 - Jan 25
-74%
$995
$262 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
View deal
Apartment Near West Side
Mar 23 - Mar 30
-8%
$508
$466 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Near West Side, Chicago, Illinois, United States
Free cancellation
View deal

Budget-friendly apartments in Chicago

Our top value vacation rentals for apartments

Apartment South Loop
from $345 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(61 ratings)
South Loop, Chicago, Illinois, United States
View deal
Apartment Gold Coast
from $142 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(3 ratings)
Gold Coast, Chicago, Illinois, United States
View deal
Apartment Near North Side
from $400 per night
Apartment ∙ 11 guests ∙ 3 bedrooms
4.4
Very good(37 ratings)
Near North Side, Chicago, Illinois, United States
View deal

Get Cozy: Apartments with Fireplace

Apartment Near West Side
Jan 5 - Jan 12
-8%
$277
$359 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Near West Side, Chicago, Illinois, United States
Free cancellation
Fireplace
View deal
Apartment Old Town
Jan 25 - Feb 1
-71%
$750
$266 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Old Town, Chicago, Illinois, United States
Free cancellation
Fireplace
View deal
Apartment Mid-North District
Dec 28 - Jan 4
-64%
$879
$323 per night
Apartment ∙ 3 guests ∙ 1 bedroom
4.0
Very good(2 ratings)
Mid-North District, Chicago, Illinois, United States
Fireplace
View deal
See all offers

Apartments with Kitchens

Apartment South Loop
Jan 4 - Jan 11
-74%
$847
$227 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Kitchen
View deal
Apartment River North
Jan 5 - Jan 12
-8%
$235
$224 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
River North, Chicago, Illinois, United States
Free cancellation
Kitchen
View deal
Apartment Ukrainian Village
Jan 5 - Jan 12
-8%
$366
$287 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
Ukrainian Village, Chicago, Illinois, United States
Free cancellation
Kitchen
View deal
See all offers

Apartments with Hot Tubs

Homes Featuring Jacuzzis and Whirlpools

Apartment Chicago Loop
Jan 18 - Jan 25
-70%
$1,918
$636 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Chicago Loop, Chicago, Illinois, United States
View deal
Apartment Goose Island
Jan 31 - Feb 7
-78%
$2,705
$563 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
Goose Island, Chicago, Illinois, United States
Free cancellation
View deal
Apartment West Town
Jan 31 - Feb 7
$609 per night
Apartment ∙ 10 guests ∙ 2 bedrooms
West Town, Chicago, Illinois, United States
Free cancellation
View deal

Information about Vacation apartments in Chicago

🏡 Apartment rentals available 3,866 rentals
💳 Possible discounts up to 64%
🌙 Nightly prices starting at $102
⭐ Popular amenities Balcony/Patio, Pool and Crib
🐾 Pet friendly homes 1,903 homes
🏊 Vacation rentals with pools 547 homes

Vacation apartments in Chicago: frequently asked questions

How much do vacation rental cost per night for Vacation apartments in Chicago?

Nightly prices for vacation home rentals in Chicago can range from $189 to $1,104 and you can find discounts up to 64%!

Is it easy to find family or group accommodations for a Vacation apartments in Chicago?

When travelling in Chicago with friends and family, consider that vacation rentals can fit an average of 5 people and are ideal for medium-sized groups and families.

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