Vacation Rentals & Apartment Rentals in Chicago

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26 apartment rentals

Great rentals within 20 miles that match your search

Distance approx 16.12 km from Chicago

(19) Excellent 

8

Just north of Chicago

Illinois / Winnetka

Winnetka cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden
“Comfortable and Convenient” Maggi greeted us pleasantly as soon as we arrived. The rental home was just as we expected. It was clean and had everything we needed for a "home base" while we visited the area. Lake Michigan is very close which is a bi
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Price per night from

$110

Responds fast!
avg. 3 hours 40 minutes

Price per night from

$110

Distance approx 12.19 km from Chicago

17

Cute, cozy modern apartment 20 min ohare and midway airports and 30 min to dt

Illinois / Melrose Park

Melrose Park apartment

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Air conditioning

Price per night from

$140

Responds fast!
avg. 5 minutes

Price per night from

$140

Distance approx 9.81 km from Chicago

11

Make It Your Own - 15 Minutes to Chicago

Illinois / Forest Park

Forest Park apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$109

Price per night from

$109

Distance approx 8.99 km from Chicago Show on Map

4

Condo

Illinois / Oak Park

Oak Park house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Air conditioning

Price per night from

$444

Price per night from

$444

Distance approx 8.88 km from Chicago

(3) Very Good 

20

Oak Park Bungalow

Illinois / Oak Park

Oak Park house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$210

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$210

Distance approx 15.39 km from Chicago

(2) Excellent 

30

Beautifully Remodeled 3 BR Townhouse near Chicago

Illinois / Wilmette

Wilmette townhouse

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$130

Responds fast!
avg. 1 hour 12 minutes

Price per night from

$130

Distance approx 12.47 km from Chicago

7

Pinewoods Retreat - Private Room

Illinois / Evanston

Evanston room

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$51

Price per night from

$51

Distance approx 17.76 km from Chicago

(1) Very Good 

24

Romantic Burr Ridge Home on 5 Manicured Acres!

Illinois / Burr Ridge

Burr Ridge house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$747

Responds fast!
avg. 55 minutes

Price per night from

$747

Distance approx 11.49 km from Chicago

12

Comfy Quarters

Illinois / River Grove

River Grove house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden

Price per night from

$90

Price per night from

$90

Distance approx 9.43 km from Chicago

(1) Excellent 

13

Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!

Illinois / Forest Park

Forest Park apartment

4 5 min stay varies

  • 4 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$149

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$149

Distance approx 8.39 km from Chicago Show on Map

24

Luxe Chicago Townhome w/ Balcony - 20 Mins to DT!

Illinois / Lincolnwood

Lincolnwood house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$110

Responds fast!
avg. 55 minutes

Price per night from

$110

Distance approx 11.91 km from Chicago

8

2 BR apartment near O'Hare

Illinois / Norridge

Norridge apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 28 mi
  • Child Friendly
  • Air conditioning

Price per night from

$90

Price per night from

$90

Distance approx 12.22 km from Chicago

9

Gorgeous garden apartment near O'Hare

Illinois / Norridge

Norridge apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 28 mi
  • Child Friendly
  • Air conditioning

Price per night from

$56

Price per night from

$56

Distance approx 12.32 km from Chicago

16

Newly Remodeled Modern Apartment

Illinois / Melrose Park

Melrose Park apartment

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly

Price per night from

$160

Responds fast!
avg. 5 minutes

Price per night from

$160

Distance approx 8.88 km from Chicago Show on Map

(1) Excellent 

14

Oak Park Beauty Sleeps 1 to 8 Guests

Illinois / Oak Park

Oak Park apartment

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$140

Responds fast!
avg. 2 hours 1 minutes

Price per night from

$140

Distance approx 11.11 km from Chicago

15

Sleep Aboard Adeline’s Sea Moose: 68 ft Private Yacht Rentals Chicago Downtown

Illinois / Lincolnwood

Lincolnwood yacht

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$1,200

Price per night from

$1,200

Distance approx 8.01 km from Chicago Show on Map

9

Cozy master bedroom in Oak Park Arts district

Illinois / Oak Park

Oak Park house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden

Price per night from

$70

Price per night from

$70

Distance approx 19.07 km from Chicago

14

Best value Beautiful, modern 4 bed, 2 bath home!

DuPage County / Lombard

Lombard house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly

Price per night from

$129

Price per night from

$129

Distance approx 5.37 km from Chicago Show on Map

(1) Excellent 

18

Handsome 3BR in Lake View by Sonder

Illinois / Lincolnwood

Lincolnwood apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$50

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$50

Distance approx 8.25 km from Chicago Show on Map

9

OAK PARK BEAUTIFUL, HISTORICAL, CONVENIENT TO PUBLIC TRANSPORTATION, AIRPORTS

Illinois / Oak Park

Oak Park b and b

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$35

Responds fast!
avg. 3 hours 44 minutes

Price per night from

$35

Distance approx 7.98 km from Chicago Show on Map

29

Elegantly Updated Albany Park 4BR/3.5BA w/ Private Fenced Yard & Garage

Illinois / Lincolnwood

Lincolnwood house

4 8 31 nights min

  • 4 bedrooms
  • sleeps 8
  • 31 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$200

Price per night from

$200

Distance approx 7.2 km from Chicago Show on Map

24

Opulent Historic 2BR Apartment in Andersonville w/ Contemporary Kitchen

Illinois / Lincolnwood

Lincolnwood apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$118

Price per night from

$118

Distance approx 10.91 km from Chicago

8

Real 15 Min to City & McCormick Place. See Ad for Details. Quiet Safe Area. View

Illinois / Summit

Summit apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$150

Price per night from

$150

Distance approx 5.37 km from Chicago Show on Map

23

Vintage 3BR in Lake View by Sonder

Illinois / Lincolnwood

Lincolnwood apartment

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$50

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$50

Distance approx 10.59 km from Chicago

22

Hull Chateau

Illinois / Evanston

Evanston house

2 7 1 night min

  • 2 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 2 mi
  • Child Friendly
  • Car not necessary

Price per night from

$222

Price per night from

$222

Distance approx 5.24 km from Chicago Show on Map

21

Grand 3BR in Roscoe Village by Sonder

Illinois / Lincolnwood

Lincolnwood condo

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$117

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$117

About Chicago

Affixed by stunning Lake Michigan and laden with awe-inspiring architecture, Chicago is more than just a big city. Besides its vibrant downtown area, which includes some of the tallest buildings in the world, Chicago has 26 miles of uninterrupted lakefront, hundreds of lively parks and 77 unique neighborhoods. It's this truly distinctive mix of incredible attractions and cultural allure that make Chicago one of the friendliest, most livable cities in America.

Chicago's neighborhoods represent more than 100 countries, and it's through this diversity and profound international culture that we are able to develop the country's best restaurants, theaters and museums.

Chicago has also developed a reputation as a must-visit destination for foodies. In fact, Chicago is one of only three cities in the country to have its culinary chops rated by the Michelin Guide, and in 2015, Chicago will have the honor to host the prestigious James Beard Awards for the first time in the foundation’s 25 year history.

With incredible shopping on The Magnificent Mile, world premiere performances in its famed Theater District and one of the country's most active nightlife scenes, Chicago is always buzzing. The city also vaunts more than 40 museums, five regional Tony Award-winning theaters and, no matter the season, there's always a professional sports team to cheer to victory. Chicago has it all for the urban explorer to discover.

As Chicago sits squarely in the center of the country and is equipped with two major international airports, visiting is easy. From sleek downtown properties to luxury boutiques, you will discover outstanding vacation rental accommodations for every style, family size, and budget.

Cloud Gate at Millennium Park, delicious deep dish pizza and the nostalgia of Wrigley Field are all compelling enough reasons to visit Chicago, but the city's most endearing quality is its people. With classic mid-western hospitality in abundance, it's easy to feel right at home in Chicago.

Enjoy your visit to Chicago.

Information provided by: Choose Chicago