The Best Airbnb Deals in
Chicago, Illinois

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Chicago, Illinois. Enter your travel dates to find the best deals!

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AirDNA Score: 93
$169/night

Spacious Newly Built 3BR Condo Convenient Location

3 beds
2 baths
8 guests
Average Price:  
$231
27% Cheaper
than normal
AirDNA Score: 93
$75/night

Cozy Apartment with Free On-Site Parking

3 beds
1 bath
5 guests
Average Price:  
$133
44% Cheaper
than normal
AirDNA Score: 92
$240/night

Modern oasis near park, pet friendly, fast WI-FI.

3 beds
1 bath
5 guests
Average Price:  
$216
11% More
than normal
AirDNA Score: 92
$95/night

The Vanderpool House

1 bed
1 bath
4 guests
Average Price:  
$127
25% Cheaper
than normal
AirDNA Score: 89
$369/night

Chicago (Upscale Neighborhood) Multi-Unit Estate

4 beds
2.5 baths
10 guests
Average Price:  
$410
10% Cheaper
than normal
AirDNA Score: 86
$150/night

The Garden on Wayne

2 beds
1 bath
4 guests
Average Price:  
$178
16% Cheaper
than normal
AirDNA Score: 86
$219/night

Charming 2BR on Quiet Street Close to the Action

2 beds
1 bath
6 guests
Average Price:  
$312
30% Cheaper
than normal
AirDNA Score: 86
$210/night

Private In-law Suite near O''Hare

2 beds
1.5 baths
7 guests
Average Price:  
$260
19% Cheaper
than normal
AirDNA Score: 86
$115/night

3 Bedroom Vintage Hideaway In Little Italy/uic

3 beds
1 bath
6 guests
Average Price:  
$190
39% Cheaper
than normal
AirDNA Score: 86
$225/night

Dorothy''s Place 4Beds/1Bath, Free Parking

3 beds
1 bath
7 guests
Average Price:  
$252
11% Cheaper
than normal
AirDNA Score: 86
$278/night

Great location (No Chores/ No Cleaning Fees)

3 beds
1 bath
5 guests
Average Price:  
$304
9% Cheaper
than normal
AirDNA Score: 86
$205/night

2 Miles to MDW 11 Miles DTWN Free Parking Wi-Fi

3 beds
2 baths
6 guests
Average Price:  
$236
13% Cheaper
than normal
AirDNA Score: 86
$175/night

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

5 beds
3 baths
10 guests
Average Price:  
$224
22% Cheaper
than normal
AirDNA Score: 86
$236/night

Newly Renovated, Spacious Urban Getaway

3 beds
2 baths
10 guests
Average Price:  
$394
40% Cheaper
than normal
AirDNA Score: 86
$124/night

High Class Apt In Uptown W/ Free Parking!

2 beds
1 bath
4 guests
Average Price:  
$221
44% Cheaper
than normal
AirDNA Score: 86
$118/night

Historic Coach House Cottage

2 beds
1 bath
4 guests
Average Price:  
$135
13% Cheaper
than normal
AirDNA Score: 86
$265/night

Chic Decor (No Chores / No Cleaning Fees)

3 beds
1 bath
6 guests
Average Price:  
$292
9% Cheaper
than normal
AirDNA Score: 86
$186/night

Cool Quiet Coach House W/ Private Access and Outdoor Space

2 beds
2 baths
6 guests
Average Price:  
$226
18% Cheaper
than normal
AirDNA Score: 86
$292/night

Amadeus Stay - Hip Central 3bdrm Apt +Free Parking

3 beds
1 bath
5 guests
Average Price:  
$327
11% Cheaper
than normal
AirDNA Score: 86
$112/night

In artistic Pilsen~Continental Breakfast~Near DWTN

2 beds
1 bath
4 guests
Average Price:  
$149
25% Cheaper
than normal
AirDNA Score: 86
$198/night

3 BDRM FREE PARK Roku TV|10 Mi. 2 Chicago Downtwn

3 beds
1.5 baths
6 guests
Average Price:  
$207
4% Cheaper
than normal
AirDNA Score: 86
$130/night

Lofty sunny basement, garage parking. Vac required

1 bed
1 bath
2 guests
Average Price:  
$124
5% More
than normal
AirDNA Score: 86
$314/night

River North''s Rock N Roll - Covd Safer, No Common Areas

2 beds
2 baths
6 guests
Average Price:  
$369
15% Cheaper
than normal
AirDNA Score: 86
$738/night

Newly Renovated 3BR East Lakeview Coach House

3 beds
2.5 baths
12 guests
Average Price:  
$543
36% More
than normal
AirDNA Score: 85
$182/night

Cozy Andersonville Cabin

1 bed
1 bath
4 guests
Average Price:  
$169
8% More
than normal
AirDNA Score: 84
$300/night

Lakeview Luxury Condo

2 beds
2 baths
4 guests
Average Price:  
$262
15% More
than normal
AirDNA Score: 83
$85/night

Handicap accessible apartment w/Level-2 EV Charger

2 beds
1 bath
5 guests
Average Price:  
$93
9% Cheaper
than normal
AirDNA Score: 80
$214/night

★★★Charming 2BR near downtown, +FREE parking★★★

2 beds
1 bath
7 guests
Average Price:  
$201
6% More
than normal
AirDNA Score: 79
$135/night

Remote Work Haven - Fast Wifi, Coffee w/KING BED

1 bed
1 bath
3 guests
Average Price:  
$127
6% More
than normal
AirDNA Score: 79
$132/night

Vintage West Town Charmer; Steps to Grand Ave Bus

3 beds
1 bath
7 guests
Average Price:  
$167
21% Cheaper
than normal
AirDNA Score: 79
$107/night

Vibrant; Studio Apartment Near Midway Airport & DT

studio
1 bath
2 guests
Average Price:  
$202
47% Cheaper
than normal
AirDNA Score: 79
$2473/night

Rock and Roll Paradise

4 beds
3.5 baths
14 guests
Average Price:  
$2680
8% Cheaper
than normal
AirDNA Score: 79
$115/night

Cozy Ukrainian Village Two Bedroom Apartment

2 beds
1 bath
4 guests
Average Price:  
$133
14% Cheaper
than normal
AirDNA Score: 79
$486/night

Million Dollar Views! Luxury Downtown Skyhouse!

3 beds
2.5 baths
6 guests
Average Price:  
$641
24% Cheaper
than normal
AirDNA Score: 79
$401/night

Pro Cleaned, Lakeview Greystone One Block from Wrigley Field

5 beds
2 baths
10 guests
Average Price:  
$408
2% Cheaper
than normal
AirDNA Score: 79
$499/night

Little Italy/UIC 3 bdrm, 2.5 bath Condo

3 beds
2.5 baths
11 guests
Average Price:  
$593
16% Cheaper
than normal
AirDNA Score: 79
$110/night

Hidden Gem in Chicago•Near Train•Parking

2 beds
1 bath
4 guests
Average Price:  
$165
33% Cheaper
than normal
AirDNA Score: 79
$347/night

NEW Beautiful & Spacious Home Outdoor Yard & Pool

3 beds
1 bath
6 guests
Average Price:  
$332
5% More
than normal
AirDNA Score: 79
$164/night

Best Location, Southport Corridor

3 beds
1 bath
6 guests
Average Price:  
$235
30% Cheaper
than normal
AirDNA Score: 79
$115/night

Contemporary 2 bedroom south facing balcony 3

2 beds
1 bath
6 guests
Average Price:  
$139
17% Cheaper
than normal
AirDNA Score: 79
$297/night

Convenient Brand New 3 Bedroom Apartment w/WIFI

3 beds
2 baths
8 guests
Average Price:  
$237
25% More
than normal
AirDNA Score: 79
$220/night

The Roscoe House near Wrigley Field

3 beds
3 baths
8 guests
Average Price:  
$522
58% Cheaper
than normal
AirDNA Score: 79
$350/night

-CHICAGO STUDIO IN JEFFERSON PARK O''HARE ROSEMONT-

studio
1 bath
3 guests
Average Price:  
$149
135% More
than normal
AirDNA Score: 79
$179/night

Huge Victorian near Loyola 2bd Apt

2 beds
1 bath
4 guests
Average Price:  
$178
1% More
than normal
AirDNA Score: 79
$180/night

Comfortable Home Base, Close to Everything!

2 beds
1 bath
4 guests
Average Price:  
$238
24% Cheaper
than normal
AirDNA Score: 79
$109/night

Andersonville Cozy 1 bedroom basement suite

1 bed
1 bath
2 guests
Average Price:  
$132
17% Cheaper
than normal
AirDNA Score: 79
$300/night

Cannabis Condo 4BR

4 beds
1 bath
8 guests
Average Price:  
$347
14% Cheaper
than normal
AirDNA Score: 79
$79/night

2BR Lakeview Condo with Deck on a Quiet Street

2 beds
1 bath
4 guests
Average Price:  
$295
73% Cheaper
than normal
AirDNA Score: 79
$362/night

Unique, Handcrafted Art Gallery Condo in River West Chicago

3 beds
2 baths
6 guests
Average Price:  
$292
24% More
than normal
AirDNA Score: 79
$84/night

Private, spacious studio in green building

1 bed
1 bath
4 guests
Average Price:  
$106
21% Cheaper
than normal
AirDNA Score: 79
$115/night

East Garfield Park 2 Bedroom

2 beds
2 baths
4 guests
Average Price:  
$124
7% Cheaper
than normal
AirDNA Score: 79
$128/night

Superb 2BR Old Town APT, PRIME LOCATION!(+Parking)

2 beds
1 bath
6 guests
Average Price:  
$235
46% Cheaper
than normal
AirDNA Score: 79
$95/night

Historic Pullman Home-Style Comfort & Great Locale

3 beds
1.5 baths
6 guests
Average Price:  
$155
39% Cheaper
than normal
AirDNA Score: 79
$125/night

Private Garden Apartment GATED FREE Parking

1 bed
1 bath
2 guests
Average Price:  
$175
29% Cheaper
than normal
AirDNA Score: 79
$95/night

Private suite in Lincoln Square

1 bed
1 bath
4 guests
Average Price:  
$113
16% Cheaper
than normal
AirDNA Score: 79
$144/night

Cool and Modern Chicago Apartment near Transit

3 beds
1 bath
5 guests
Average Price:  
$152
5% Cheaper
than normal
AirDNA Score: 79
$99/night

Logan Square Video Game Loft

studio
1 bath
4 guests
Average Price:  
$120
17% Cheaper
than normal
AirDNA Score: 79
$109/night

Sawyer Get-Away in Logan Square

2 beds
1 bath
4 guests
Average Price:  
$161
32% Cheaper
than normal
AirDNA Score: 79
$129/night

Best Location-Southport Corridor

3 beds
1 bath
6 guests
Average Price:  
$220
41% Cheaper
than normal
AirDNA Score: 79
$112/night

Great Place Garfield Park 3 Bedroom

3 beds
1 bath
10 guests
Average Price:  
$120
7% Cheaper
than normal
AirDNA Score: 79
$150/night

Chicago Living: Your Home Away From Home

1 bed
1 bath
4 guests
Average Price:  
$135
11% More
than normal
AirDNA Score: 79
$169/night

Relax in a Newly Remodeled Apartment in Irving Park

2 beds
1 bath
6 guests
Average Price:  
$211
20% Cheaper
than normal
AirDNA Score: 78
$800/night

2 Floor - 4 BR- 4Baths Condo Near downtown Chicago

4 beds
4 baths
14 guests
Average Price:  
$865
8% Cheaper
than normal
AirDNA Score: 78
$192/night

1 #11 - 2 Bedroom 1 Bath Condo - McCormick Place

2 beds
1 bath
6 guests
Average Price:  
$239
20% Cheaper
than normal
AirDNA Score: 77
$198/night

Elegant 3/BR w/Balcony by Downtown, Chinatown

3 beds
2 baths
8 guests
Average Price:  
$251
21% Cheaper
than normal
AirDNA Score: 77
$676/night

Amazing Penthouse Skyline Views!

3 beds
3 baths
14 guests
Average Price:  
$589
15% More
than normal
AirDNA Score: 77
$300/night

Paris in Chicago! Elegant vintage apartment.

2 beds
1 bath
4 guests
Average Price:  
$313
4% Cheaper
than normal
AirDNA Score: 77
$200/night

Ukrainian Village 3 Bedroom Apartment

3 beds
1 bath
5 guests
Average Price:  
$222
10% Cheaper
than normal
AirDNA Score: 77
$458/night

Chic Downtown Condo - Heart of River North!

2 beds
2 baths
6 guests
Average Price:  
$431
6% More
than normal
AirDNA Score: 76
$249/night

Near 606 Trail | Free Garage Parking | W&D |LUXTEL

3 beds
1 bath
7 guests
Average Price:  
$251
1% Cheaper
than normal
AirDNA Score: 76
$175/night

Logan Square/Bucktown - Close to Everything

2 beds
1 bath
4 guests
Average Price:  
$212
17% Cheaper
than normal
AirDNA Score: 76
$122/night

West of Loop 2bdrm Apartment

2 beds
1 bath
4 guests
Average Price:  
$124
2% Cheaper
than normal
AirDNA Score: 75
$90/night

Cozy Bungalow Getaway

1 bed
1 bath
2 guests
Average Price:  
$119
24% Cheaper
than normal
AirDNA Score: 75
$599/night

♥ 3BR/2.5 BA House + Roof Deck in Wicker Park ♥

3 beds
2.5 baths
12 guests
Average Price:  
$723
17% Cheaper
than normal
AirDNA Score: 75
$289/night

As seen on NBC’s hit series, “Chicago Fire!”

2 beds
2 baths
7 guests
Average Price:  
$342
15% Cheaper
than normal
AirDNA Score: 74
$175/night

Old Irving Park 2 bd/1 ba, 20 mins to Downtown

2 beds
1 bath
6 guests
Average Price:  
$191
8% Cheaper
than normal
AirDNA Score: 74
$168/night

1 Bed Coach House\Full Kitchen&Bath

1 bed
1 bath
2 guests
Average Price:  
$187
10% Cheaper
than normal
AirDNA Score: 74
$221/night

Lincoln Park 1BD/1BA Apt (1f)

1 bed
1 bath
4 guests
Average Price:  
$256
14% Cheaper
than normal
AirDNA Score: 74
$117/night

Classic BuckTown with Backyard & Garage Parking.

3 beds
1 bath
6 guests
Average Price:  
$273
57% Cheaper
than normal
AirDNA Score: 74
$198/night

Modern Chicago Home Away from Home

2 beds
1 bath
6 guests
Average Price:  
$226
12% Cheaper
than normal
AirDNA Score: 73
$275/night

Soft Leather & Warm Bricks in Stylish New Home

3 beds
2 baths
5 guests
Average Price:  
$359
23% Cheaper
than normal
AirDNA Score: 73
$285/night

Historic 1920s bungalow near Logan Square !

3 beds
2 baths
7 guests
Average Price:  
$369
23% Cheaper
than normal
AirDNA Score: 73
$195/night

NEW! 2 BDRM | 10mi. 2 Downtown |Free Parking| WIFI

2 beds
1 bath
2 guests
Average Price:  
$207
6% Cheaper
than normal
AirDNA Score: 73
$169/night

Bucktown Private GEM - a 3BR Modern Oasis

3 beds
2.5 baths
10 guests
Average Price:  
$276
39% Cheaper
than normal
AirDNA Score: 73
$187/night

Bronzeville Apartment

3 beds
1 bath
6 guests
Average Price:  
$240
22% Cheaper
than normal
AirDNA Score: 73
$110/night

Welcome to The Mayfair Garden !

1 bed
1 bath
2 guests
Average Price:  
$135
19% Cheaper
than normal
AirDNA Score: 72
$127/night

Bucktown Bungalow-Prime location w/parking!

1 bed
1 bath
6 guests
Average Price:  
$195
35% Cheaper
than normal
AirDNA Score: 72
$200/night

Ukrainian Village 6 Room Apartment

3 beds
1 bath
6 guests
Average Price:  
$162
23% More
than normal
AirDNA Score: 72
$150/night

RIVER NORTH MODERN POOL/SPA DOWNTOWN

1 bed
1 bath
2 guests
Average Price:  
$250
40% Cheaper
than normal
AirDNA Score: 72
$124/night

Hidden Gem in South Logan Square

1 bed
1 bath
3 guests
Average Price:  
$175
29% Cheaper
than normal
AirDNA Score: 71
$82/night

Bright 2br Apt W/ Private Entrance & Laundry

2 beds
1 bath
6 guests
Average Price:  
$116
29% Cheaper
than normal
AirDNA Score: 71
$218/night

Contemporary, pet friendly, convenient parking

2 beds
1 bath
5 guests
Average Price:  
$222
2% Cheaper
than normal
AirDNA Score: 71
$82/night

The Hobbit Hole

studio
1 bath
4 guests
Average Price:  
$68
21% More
than normal
AirDNA Score: 71
$89/night

Designer 2BR in Converted Uptown Firehouse

2 beds
2 baths
4 guests
Average Price:  
$236
62% Cheaper
than normal
AirDNA Score: 71
$98/night

1 Bedroom Apartment In Historic Old Town House

1 bed
1 bath
3 guests
Average Price:  
$115
15% Cheaper
than normal
AirDNA Score: 71
$118/night

Cozy and Private Andersonville Retro Studio

studio
1 bath
2 guests
Average Price:  
$177
33% Cheaper
than normal
AirDNA Score: 71
$230/night

Private studio with free garage parking

studio
1 bath
3 guests
Average Price:  
$187
23% More
than normal
AirDNA Score: 71
$70/night

Long Term Rental - a Great Place to Call Home

1 bed
1 bath
3 guests
Average Price:  
$73
4% Cheaper
than normal
AirDNA Score: 71
$265/night

Decompress on a Sophisticated Chaise at a Glamorous Hideaway

1 bed
1 bath
3 guests
Average Price:  
$305
13% Cheaper
than normal
AirDNA Score: 71
$143/night

Bucktown''s Best Bang for the Buck

2 beds
1 bath
5 guests
Average Price:  
$141
1% More
than normal