Vacation Condo Rental in Chicago - HomeToGo base64Hash Vacation Condo Rental in Chicago - HomeToGo

Vacation Condo Rental in Chicago

Anytime
1 guest
Anytime
1 guest

  • Price per night

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

  • Accommodation types

    • Condo
    • Cabin
    • House

  • 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
    • Parking
    • Kitchen
    • TV
    • Air conditioning
    • Balcony/patio
    • Washing machine
    • Microwave
    • Hot tub
    • Fireplace
    • Dishwasher
    • Yard
    • Sauna
    • Crib
    Show more

  • Accommodation type

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

  • Activities

    • Grill
    • Fishing

Condo rentals in Chicago: Recommended rentals

Condo rentals in Chicago: find your perfect rental from just $83 per night!

Condo West Lakeview
Mar 3 - Mar 10
Condo ∙ 8 guests ∙ 4 bedrooms

Fully Equipped Condo | Good for Workation

West Lakeview, Chicago, Illinois, United States
$214
per night
Outstanding(82 ratings)
$214
per night
View deal
Condo Rogers Park
-55%
Mar 3 - Mar 10
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with Garden & Patio | City View

Rogers Park, Chicago, Illinois, United States
$411$226
per night
Excellent(38 ratings)
$411$226
per night
View deal
Condo Lake View
May 28 - Jun 4
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Patio

Lake View, Chicago, Illinois, United States
$395
per night
Outstanding(16 ratings)
$395
per night
View deal
Condo Pulaski Park
-67%
Feb 15 - Feb 22
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with 3 Rooms for 8 Persons

Pulaski Park, West Town, Chicago
$422$304
per night
Very good(10 ratings)
$422$304
per night
View deal
Condo Wicker Park
Mar 3 - Mar 10
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with Patio

Wicker Park, Chicago, Illinois, United States
$307
per night
Outstanding(7 ratings)
$307
per night
View deal
Condo Woodlawn
Mar 3 - Mar 10
Condo ∙ 6 guests ∙ 3 bedrooms

Family-Friendly Condo | Suitable for Remote Work

Woodlawn, Chicago, Illinois, United States
$465
per night
Outstanding(4 ratings)
$465
per night
View deal
Condo Grand Boulevard
Mar 3 - Mar 10
Condo ∙ 4 guests ∙ 2 bedrooms

Condo | City View | Perfect for Remote Work

Grand Boulevard, Chicago, Illinois, United States
$210
per night
Outstanding(28 ratings)
$210
per night
View deal
Condo Bucktown
Jun 28 - Jul 5
Condo ∙ 8 guests ∙ 3 bedrooms

Fully Equipped Nice Condo with Terrace

Bucktown, Chicago, Illinois, United States
$372
per night
Outstanding(36 ratings)
$372
per night
View deal
Condo West Lakeview
May 28 - Jun 4
Condo ∙ 12 guests ∙ 3 bedrooms

Fully Equipped Condo | City View | Pets Allowed

West Lakeview, Chicago, Illinois, United States
$602
per night
Outstanding(16 ratings)
$602
per night
View deal
Condo River North
-70%
Mar 3 - Mar 10
Condo ∙ 8 guests ∙ 4 bedrooms

Condo | Near John Hancock Center

River North, Chicago, Illinois, United States
$1,233$458
per night
Outstanding(68 ratings)
$1,233$458
per night
View deal
Condo Old Town Triangle
Mar 8 - Mar 15
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with 2 Rooms for 4 Persons

Old Town Triangle, Chicago, Illinois, United States
$492
per night
Very good(36 ratings)
$492
per night
View deal
Condo Rogers Park
-58%
Mar 3 - Mar 10
Condo ∙ 6 guests ∙ 3 bedrooms

Condo | Perfect for Remote Work

Rogers Park, Chicago, Illinois, United States
$316$244
per night
Excellent(28 ratings)
$316$244
per night
View deal
Condo Lake View
Jan 18 - Jan 25
Condo ∙ 10 guests ∙ 3 bedrooms

Children-Friendly Condo with BBQ, Garden & Patio | Pets Are Welcome

Lake View, Chicago, Illinois, United States
$500
per night
Outstanding(134 ratings)
$500
per night
View deal
Condo Lake View East
May 28 - Jun 4
Condo ∙ 4 guests ∙ 1 bedroom

Condo with 1 Room for 4 Persons

Lake View East, Chicago, Illinois, United States
$244
per night
Excellent(21 ratings)
$244
per night
View deal
Condo Near West Side
-85%
Feb 22 - Mar 1
Free cancellation
Condo ∙ 6 guests ∙ 2 bedrooms

Fully Equipped Nice Condo with Garden

Near West Side, Chicago, Illinois, United States
$535$128
per night
Outstanding(7 ratings)
$535$128
per night
View deal
Show all 364 properties

Popular amenities for Condo rentals in Chicago

Find the perfect home for your stay

Condos with internet

Condos with internet

Condos with pools

Condos with pools

Condos with parking

Condos with parking

Pet-Friendly Condos

Pet-Friendly Condos

Top-rated condos in Chicago

Browse our top rated condos offers

Condo Armour Square
Jul 12 - Jul 19
$431
per night
Condo ∙ 13 guests ∙ 5 bedrooms

Condo with 5 rooms for 13 persons

4.5
Excellent(21 ratings)
Armour Square, Chicago, Illinois, United States
View deal
Condo Noble Square
Jun 22 - Jun 29
$539
per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with yard & terrace | Good for workation

5.0
Outstanding(53 ratings)
Noble Square, Chicago, Illinois, United States
View deal
Condo Lake View East
Mar 18 - Mar 25
$588
per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with 3 rooms for 7 persons

4.7
Excellent(26 ratings)
Lake View East, Chicago, Illinois, United States
View deal

Best Deals and Discounts on Condos

Save up to 79%

Condo Rogers Park
Feb 1 - Feb 8
-66%
$312
$231
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Patio | Perfect for Remote Work

4.7
Excellent(23 ratings)
Rogers Park, Chicago, Illinois, United States
View deal
Condo West Loop
Feb 1 - Feb 8
-66%
$508
$362
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo | City View

5.0
Outstanding(23 ratings)
West Loop, Chicago, Illinois, United States
View deal
Condo Old Town
Feb 2 - Feb 9
-79%
$2,855
$817
per night
Condo ∙ 16 guests ∙ 8 bedrooms

Condo with 8 Rooms for 16 Persons

4.7
Excellent(19 ratings)
Old Town, Chicago, Illinois, United States
Free cancellation
View deal

Budget-friendly condos in Chicago

Our top value vacation rentals for condos

Condo Grand Boulevard
Jun 21 - Jun 28
-21%
$299
$246
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with barbecue & terrace

4.8
Outstanding(7 ratings)
Grand Boulevard, Chicago, Illinois, United States
View deal
Condo Lake View East
Mar 3 - Mar 10
-66%
$466
$466
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-oriented condo with terrace | Good for workation

4.9
Outstanding(54 ratings)
Lake View East, Chicago, Illinois, United States
View deal
Condo Roscoe Village
Jun 21 - Jun 28
$415
per night
Condo ∙ 10 guests ∙ 5 bedrooms

Fully equipped condo

3.6
Good(50 ratings)
Roscoe Village, Chicago, Illinois, United States
View deal

Condos with Balconies

Condo Lake View
Sep 19 - Sep 26
-27%
$475
$370
per night
Condo ∙ 5 guests ∙ 2 bedrooms

Children-friendly big condo | Good for workation

5.0
Outstanding(12 ratings)
Lake View, Chicago, Illinois, United States
Balcony
View deal
Condo East Village
Sep 19 - Sep 26
$634
per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with patio & BBQ | Suitable for remote work

East Village, Chicago, Illinois, United States
Balcony
View deal
Condo Lincoln Park
Sep 19 - Sep 26
$506
per night
Condo ∙ 8 guests ∙ 5 bedrooms

Family-friendly condo with garden & patio

4.8
Outstanding(37 ratings)
Lincoln Park, Chicago, Illinois, United States
Balcony
View deal
See all offers

Soak Up the Sun: Condos with Patios

Condo Lincoln Park
Sep 19 - Sep 26
$315
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Child-friendly condo with BBQ & terrace | City view | Good for workation | Pets allowed

4.9
Outstanding(100 ratings)
Lincoln Park, Chicago, Illinois, United States
Balcony/Patio
View deal
Condo Old Town Triangle
Sep 19 - Sep 26
-27%
$357
$269
per night
Condo ∙ 3 guests ∙ 1 bedroom

Condo with terrace

4.8
Outstanding(34 ratings)
Old Town Triangle, Chicago, Illinois, United States
Balcony/Patio
View deal
Condo Lake View East
Sep 16 - Sep 23
-24%
$389
$212
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped lovely condo | Lake view

5.0
Outstanding(2 ratings)
Lake View East, Chicago, Illinois, United States
Balcony/Patio
View deal
See all offers

Browse Pet-friendly Condos

Condo Wrigleyville
Sep 19 - Sep 26
$592
per night
Condo ∙ 9 guests ∙ 4 bedrooms

Condo | Pet-friendly

Wrigleyville, Chicago, Illinois, United States
Pet-friendly
View deal
Condo Rogers Park
Aug 2 - Aug 9
$265
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, yard & hot tub | Lake view

4.8
Outstanding(214 ratings)
Rogers Park, Chicago, Illinois, United States
Pet-friendly
View deal
Condo Central Station
Jun 28 - Jul 5
$488
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with patio & barbeque

4.7
Excellent(38 ratings)
Central Station, Chicago, Illinois, United States
Pet-friendly
View deal
See all offers

Condos with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Condo West Town
Jul 22 - Jul 29
$257
per night
Condo ∙ 5 guests ∙ 2 bedrooms

Family-friendly condo with patio, yard & hot tub | City view | Pets allowed

5.0
Outstanding(225 ratings)
West Town, Chicago, Illinois, United States
View deal
Condo Rogers Park
Feb 19 - Feb 26
$297
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped condo with garden, barbeque & jacuzzi | Nature view | Pets are welcome

4.9
Outstanding(243 ratings)
Rogers Park, Chicago, Illinois, United States
View deal
Condo Near West Side
Mar 16 - Mar 23
$237
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with patio & jacuzzi | City view | Perfect for remote work

5.0
Outstanding(17 ratings)
Near West Side, Chicago, Illinois, United States
View deal

Condos in Chicago for Any Type of Traveler

Looking for cabins to accommodate a large group in Chicago?

HomeToGo offers numerous Condos in Chicago with 7+ bedrooms and seven or more bathrooms. Find amazing Condos for big groups in Chicago, complete with private pool, large kitchen, and plenty of space to relax. January is the most affortable time to stay in Chicago with a large group, when nightly prices for Condos will range from $219 to $1,015 per night. Begin browsing the top cabins for 8+ people and plan the perfect trip!

Searching for a remote vacation in Chicago with your loved one?

Book amazing Condos in Chicago for a romantic trip, complete with jacuzzi, sauna, and a wonderful view of Chicago's stunning scenery. There are many relaxing things to try with your partner on your private trip, including swimming, hiking, biking, and many other outdoor activities. The most affordable time to book is January with prices starting at $83 per day. Search HomeToGo's best Condos for couples in Chicago now!

Information about Condo rentals in Chicago

🏡 Condos available 364 rentals
💳 Possible discounts up to 66%
🌙 Nightly prices starting at $83
⭐ Popular amenities Non-smoking, Internet and Air conditioning
🐾 Pet friendly homes 112 homes

Condo rentals in Chicago: frequently asked questions

Condo rentals in Chicago: What is the nightly cost of a stay?

HomeToGo has ideal vacation rentals, with rates as low as $83 per night.

Condo rentals in Chicago: can I find a vacation rental suitable for a large group?

Usually the average Condo size is 195 m² and can fit 7 people on average which is ideal for large groups.

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