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
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