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
$197/night
Spacious Newly Built 3BR Condo Convenient Location
3 beds
2 baths
8 guests
Average Price:
$231
15% Cheaper
than normal
AirDNA Score: 92
$241/night
Modern oasis near park, pet friendly, fast WI-FI.
3 beds
1 bath
5 guests
Average Price:
$221
9% More
than normal
AirDNA Score: 89
$409/night
Chicago (Upscale Neighborhood) Multi-Unit Estate
4 beds
2.5 baths
10 guests
Average Price:
$412
1% Cheaper
than normal
AirDNA Score: 86
$147/night
A+Posh Chicago Home Roscoe Village Wrigley Classic
1 bed
1 bath
2 guests
Average Price:
$183
20% 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:
$339
35% Cheaper
than normal
AirDNA Score: 86
$172/night
2 Miles to MDW 11 Miles DTWN Free Parking Wi-Fi
3 beds
2 baths
6 guests
Average Price:
$238
28% Cheaper
than normal
AirDNA Score: 86
$350/night
3 Bedroom Vintage Hideaway In Little Italy/uic
3 beds
1 bath
6 guests
Average Price:
$225
56% More
than normal
AirDNA Score: 86
$320/night
Location! Close to Fulton Mkt & Downtown 2 bedroom
2 beds
1 bath
7 guests
Average Price:
$229
40% More
than normal
AirDNA Score: 86
$1150/night
Come Together in This Vibrant Restored Mansion near Wrigley
6 beds
3.5 baths
16 guests
Average Price:
$1211
5% Cheaper
than normal
AirDNA Score: 86
$123/night
Historic Coach House Cottage
2 beds
1 bath
4 guests
Average Price:
$139
12% Cheaper
than normal
AirDNA Score: 86
$387/night
Peaceful River West Apt with free parking
2 beds
1 bath
4 guests
Average Price:
$248
56% More
than normal
AirDNA Score: 86
$433/night
Wrigley Oasis! Steps from the Field! - 3BR/1BA!
3 beds
1 bath
6 guests
Average Price:
$360
20% More
than normal
AirDNA Score: 86
$210/night
Private In-law Suite near O''Hare
2 beds
1.5 baths
7 guests
Average Price:
$255
18% Cheaper
than normal
AirDNA Score: 85
$252/night
Comfy River West Apt with Free Parking
2 beds
1 bath
4 guests
Average Price:
$205
23% More
than normal
AirDNA Score: 85
$120/night
Ina's Beachwood Inn In the Heart of Wicker Park
1 bed
1 bath
6 guests
Average Price:
$106
13% More
than normal
AirDNA Score: 85
$700/night
WrigleyVilla - 1/2 Block From Wrigley Field!
3 beds
1 bath
10 guests
Average Price:
$703
0% Cheaper
than normal
AirDNA Score: 85
$161/night
AirDNA Score: 84
$273/night
NEW rehab LOGAN Sq TOP FLOOR free laundry SUNNY
3 beds
1 bath
8 guests
Average Price:
$240
14% More
than normal
AirDNA Score: 84
$204/night
Explore Lincoln Park from a Polished Apartment
1 bed
1 bath
4 guests
Average Price:
$233
12% Cheaper
than normal
AirDNA Score: 81
$487/night
Historic lux Townhouse on Chicago's Gold Coast
4 beds
3.5 baths
10 guests
Average Price:
$660
26% Cheaper
than normal
AirDNA Score: 80
$253/night
★★★Charming 2BR near downtown, +FREE parking★★★
2 beds
1 bath
6 guests
Average Price:
$224
13% More
than normal
AirDNA Score: 80
$837/night
The Palmer Home In Logan Square: original listing
4 beds
3 baths
12 guests
Average Price:
$896
7% Cheaper
than normal
AirDNA Score: 80
$221/night
Edgewater Glen Suite in Historical Home
1 bed
1 bath
2 guests
Average Price:
$151
46% More
than normal
AirDNA Score: 79
$134/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
$2359/night
Rock and Roll Paradise
4 beds
3.5 baths
14 guests
Average Price:
$2806
16% Cheaper
than normal
AirDNA Score: 79
$146/night
Cool! 2nd Story Loft. BEST Location! Super CLEAN!
studio
1 bath
2 guests
Average Price:
$154
5% Cheaper
than normal
AirDNA Score: 79
$458/night
*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
4 beds
2 baths
10 guests
Average Price:
$420
9% More
than normal
AirDNA Score: 79
$250/night
Garden Apartment in Historic Hyde Park Mansion
2 beds
2 baths
5 guests
Average Price:
$252
1% Cheaper
than normal
AirDNA Score: 79
$110/night
'Secret Garden' Apartment in Wrigleyville
1 bed
1 bath
2 guests
Average Price:
$140
21% Cheaper
than normal
AirDNA Score: 79
$328/night
AirDNA Score: 79
$145/night
Private, Charming, Coach House Loft in Andersonville
studio
1 bath
2 guests
Average Price:
$173
16% Cheaper
than normal
AirDNA Score: 79
$247/night
Spacious & Stylish Home at the ♥ of Wicker Park
3 beds
2.5 baths
16 guests
Average Price:
$401
38% Cheaper
than normal
AirDNA Score: 79
$198/night
Relax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village
1 bed
1 bath
4 guests
Average Price:
$180
10% More
than normal
AirDNA Score: 79
$94/night
Spacious 1BR apartment in a central location
1 bed
1 bath
3 guests
Average Price:
$95
1% Cheaper
than normal
AirDNA Score: 79
$891/night
Million Dollar Views! Luxury Downtown Skyhouse!
3 beds
2.5 baths
6 guests
Average Price:
$596
49% More
than normal
AirDNA Score: 79
$535/night
Little Italy/UIC 3 bdrm, 2.5 bath Condo
3 beds
2.5 baths
11 guests
Average Price:
$625
14% Cheaper
than normal
AirDNA Score: 79
$527/night
NEW Beautiful & Spacious Home Outdoor Yard & Pool
3 beds
1 bath
4 guests
Average Price:
$383
38% More
than normal
AirDNA Score: 79
$252/night
Best location in Chicago! Superhost
1 bed
1 bath
3 guests
Average Price:
$260
3% Cheaper
than normal
AirDNA Score: 79
$138/night
Garden Apartment in the Historic Heart of the City
1 bed
1 bath
3 guests
Average Price:
$115
20% More
than normal
AirDNA Score: 79
$250/night
Wrigleyville 75 yards from Wrigley Field
2 beds
1 bath
10 guests
Average Price:
$427
41% Cheaper
than normal
AirDNA Score: 79
$191/night
Pro Cleaned & Isolated West Loop Coach House
1 bed
1 bath
3 guests
Average Price:
$129
48% More
than normal
AirDNA Score: 79
$145/night
Lovely City Apartment Near Downtown-Food-Train
2 beds
1 bath
5 guests
Average Price:
$155
6% Cheaper
than normal
AirDNA Score: 79
$110/night
Whole Flat in Private Club. Walk to L, Dining & Shows
1 bed
1 bath
4 guests
Average Price:
$183
40% Cheaper
than normal
AirDNA Score: 79
$110/night
East Garfield Park 2 Bedroom
2 beds
2 baths
4 guests
Average Price:
$124
11% Cheaper
than normal
AirDNA Score: 79
$106/night
Historic East Village in West Town
1 bed
1 bath
4 guests
Average Price:
$120
12% Cheaper
than normal
AirDNA Score: 79
$144/night
Entire place with free parking.
studio
1 bath
4 guests
Average Price:
$87
66% More
than normal
AirDNA Score: 78
$535/night
Duplex Near the Beach! 3 Bedrooms In Andersonville
3 beds
2 baths
6 guests
Average Price:
$238
125% More
than normal
AirDNA Score: 78
$200/night
1 #11 - 2 Bedroom 1 Bath Condo - McCormick Place
2 beds
1 bath
6 guests
Average Price:
$233
14% Cheaper
than normal
AirDNA Score: 78
$450/night
Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
4 beds
3 baths
16 guests
Average Price:
$786
43% Cheaper
than normal
AirDNA Score: 77
$146/night
Clean, Cozy, Comfortable Studio Near Downtown
studio
1 bath
2 guests
Average Price:
$95
54% More
than normal
AirDNA Score: 77
$239/night
Elegant 3/BR w/Balcony by Downtown, Chinatown
3 beds
2 baths
8 guests
Average Price:
$251
5% Cheaper
than normal
AirDNA Score: 77
$360/night
Amazing Penthouse Skyline Views!
3 beds
3 baths
14 guests
Average Price:
$616
42% Cheaper
than normal
AirDNA Score: 75
$303/night
Trendy Wicker Park Loft with Parking
3 beds
2 baths
8 guests
Average Price:
$293
3% More
than normal
AirDNA Score: 75
$350/night
Wrigleyville townhome two blocks from ballpark
2 beds
1 bath
4 guests
Average Price:
$350
0% Cheaper
than normal
AirDNA Score: 75
$815/night
♥ 3BR/2.5 BA House + Roof Deck in Wicker Park ♥
3 beds
2.5 baths
12 guests
Average Price:
$586
39% More
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:
$193
9% Cheaper
than normal
AirDNA Score: 74
$168/night
1 Bed Coach House\Full Kitchen&Bath
1 bed
1 bath
2 guests
Average Price:
$192
12% Cheaper
than normal
AirDNA Score: 74
$310/night
Lincoln Park 1BD/1BA Apt (1f)
1 bed
1 bath
4 guests
Average Price:
$255
22% More
than normal
AirDNA Score: 73
$359/night
Historic 1920s bungalow near Logan Square !
3 beds
2 baths
7 guests
Average Price:
$370
3% Cheaper
than normal
AirDNA Score: 73
$195/night
Highly Rated, Equip for Long Stays, Wicker Park
1 bed
1 bath
2 guests
Average Price:
$245
20% Cheaper
than normal
AirDNA Score: 73
$98/night
Charming Edgewater/Andersonville Garden 1 bdrm.
1 bed
1 bath
3 guests
Average Price:
$104
6% Cheaper
than normal
AirDNA Score: 73
$210/night
Hyde Park/ Bronzeville Apartment 3E
3 beds
1 bath
6 guests
Average Price:
$238
12% Cheaper
than normal
AirDNA Score: 72
$1599/night
One Of A Kind Luxe Logan Square Home 8BR/5.5BA/PK!
8 beds
5.5 baths
16 guests
Average Price:
$1844
13% Cheaper
than normal
AirDNA Score: 72
$181/night
Bucktown Bungalow-Prime location w/parking!
1 bed
1 bath
6 guests
Average Price:
$207
13% Cheaper
than normal
AirDNA Score: 72
$255/night
Beautiful Luxury Loft in Fulton Market, Sleeps 12
2 beds
2 baths
12 guests
Average Price:
$528
52% Cheaper
than normal
AirDNA Score: 72
$1132/night
The Cortland In Logan Square 4BR/3BA w/Parking!
4 beds
3 baths
16 guests
Average Price:
$1670
32% Cheaper
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
$363/night
Vintage Downtown Penthouse, Safe #6 +gym&balcony
2 beds
1.5 baths
8 guests
Average Price:
$308
18% More
than normal
AirDNA Score: 71
$115/night
Humboldt Park Traveler's Lodge
studio
1 bath
3 guests
Average Price:
$117
2% Cheaper
than normal
AirDNA Score: 71
$831/night
Stunning Old Town Penthouse with Private Rooftop
5 beds
4 baths
10 guests
Average Price:
$856
3% Cheaper
than normal
AirDNA Score: 71
$179/night
Bright 2br Apt W/ Private Entrance & Laundry
2 beds
1 bath
5 guests
Average Price:
$140
28% More
than normal
AirDNA Score: 71
$676/night
Luxe 6BR House *Trendy Logan Square *Garage Access
6 beds
3.5 baths
16 guests
Average Price:
$747
10% Cheaper
than normal
AirDNA Score: 71
$250/night
Private studio with free garage parking
studio
1 bath
3 guests
Average Price:
$178
40% More
than normal
AirDNA Score: 71
$181/night
Hear the Crowd Roar from a Condo Moments Away from Wrigley
3 beds
1 bath
10 guests
Average Price:
$314
42% Cheaper
than normal
AirDNA Score: 71
$287/night
Sophisticated River West 2 Bedroom - Near the L
2 beds
2 baths
6 guests
Average Price:
$177
62% More
than normal
AirDNA Score: 71
$218/night
Contemporary, pet friendly, convenient parking
2 beds
1 bath
5 guests
Average Price:
$216
1% More
than normal
AirDNA Score: 71
$107/night
The Banksy-Greystone Rooftop Firepit United Center
2 beds
1 bath
6 guests
Average Price:
$186
42% Cheaper
than normal
AirDNA Score: 71
$246/night
Bright 2 Bedroom In Bucktown with Vintage Charm
2 beds
1 bath
6 guests
Average Price:
$152
62% More
than normal
AirDNA Score: 71
$83/night
Sweet Spacious Suite: Country in the City
1 bed
1 bath
4 guests
Average Price:
$78
6% More
than normal
AirDNA Score: 71
$287/night
Decompress on a Sophisticated Chaise at a Glamorous Hideaway
1 bed
1 bath
3 guests
Average Price:
$328
12% Cheaper
than normal
AirDNA Score: 71
$120/night
Great location, private entry and patio!
1 bed
1 bath
5 guests
Average Price:
$145
17% Cheaper
than normal
AirDNA Score: 71
$99/night
The Avondale Garden Unit
2 beds
1 bath
4 guests
Average Price:
$119
17% Cheaper
than normal
AirDNA Score: 71
$200/night
Art filled apartment in Logan
3 beds
1 bath
6 guests
Average Price:
$245
18% Cheaper
than normal
AirDNA Score: 71
$109/night
Spacious & private! Free parking! Great location!
studio
1 bath
2 guests
Average Price:
$147
26% Cheaper
than normal
AirDNA Score: 71
$140/night
Unique, comfortable oasis in the city
2 beds
1 bath
4 guests
Average Price:
$147
5% Cheaper
than normal
AirDNA Score: 71
$211/night
Visit United Center & Explore The City of Chicago
2 beds
1 bath
4 guests
Average Price:
$183
15% More
than normal
AirDNA Score: 71
$148/night
Dugout in Wrigleyville
studio
1 bath
4 guests
Average Price:
$155
5% Cheaper
than normal
AirDNA Score: 71
$193/night
Warm&Spacious 2Br Apt by CTA Blue, Easy Parking!
2 beds
1 bath
4 guests
Average Price:
$156
24% More
than normal
AirDNA Score: 71
$135/night
Dream Condo steps from Wrigley Field!
2 beds
1 bath
7 guests
Average Price:
$271
50% Cheaper
than normal
AirDNA Score: 71
$314/night
Secret Gallery on the Park - 2bd/1ba + 1bd/1ba
3 beds
2 baths
8 guests
Average Price:
$324
3% Cheaper
than normal
AirDNA Score: 71
$285/night
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
3 beds
2 baths
5 guests
Average Price:
$403
29% Cheaper
than normal
AirDNA Score: 71
$722/night
Beautiful Spacious RiverWest Townhome 4-Bed/4-Bath
4 beds
3.5 baths
8 guests
Average Price:
$1134
36% Cheaper
than normal
AirDNA Score: 71
$626/night
Spacious Five Bedroom Home in Trendy Chicago Neighborhood
5 beds
3.5 baths
15 guests
Average Price:
$644
3% Cheaper
than normal
AirDNA Score: 70
$144/night
MODERN LOFT Downtown by McCormick w/KING BED WiFi
1 bed
1 bath
3 guests
Average Price:
$165
13% Cheaper
than normal
AirDNA Score: 70
$340/night
The Bucktown House - Damen Suite - Since 2008
3 beds
2 baths
8 guests
Average Price:
$335
1% More
than normal
AirDNA Score: 69
$114/night
2 bedroom apartment near train line and bus lines!
2 beds
1 bath
8 guests
Average Price:
$108
6% More
than normal
AirDNA Score: 69
$900/night
711 The Penthouse
5 beds
2.5 baths
16 guests
Average Price:
$1275
29% Cheaper
than normal
AirDNA Score: 68
$307/night
3-3A - 3 Bedroom Condo with Parking - McCormick Pl
3 beds
2 baths
9 guests
Average Price:
$324
5% Cheaper
than normal
AirDNA Score: 68
$96/night
Attic apartment in a hip neighborhood!
studio
1 bath
2 guests
Average Price:
$105
9% Cheaper
than normal
AirDNA Score: 68
$153/night
Beautiful European Apartment
3 beds
1 bath
6 guests
Average Price:
$169
9% Cheaper
than normal