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:  
$249
32% Cheaper
than normal
AirDNA Score: 92
$210/night

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

3 beds
1 bath
4 guests
Average Price:  
$217
3% Cheaper
than normal
AirDNA Score: 92
$91/night

The Vanderpool House

1 bed
1 bath
4 guests
Average Price:  
$132
31% Cheaper
than normal
AirDNA Score: 89
$345/night

Chicago (Upscale Neighborhood) Multi-Unit Estate

4 beds
2.5 baths
10 guests
Average Price:  
$442
22% Cheaper
than normal
AirDNA Score: 88
$108/night

Royal Coach House Cottage

1 bed
1 bath
4 guests
Average Price:  
$133
19% Cheaper
than normal
AirDNA Score: 87
$109/night

Spacious, light-drenched studio-private entrance!

studio
1.5 baths
2 guests
Average Price:  
$143
24% Cheaper
than normal
AirDNA Score: 86
$108/night

Historic Coach House Cottage

1 bed
1 bath
4 guests
Average Price:  
$138
22% Cheaper
than normal
AirDNA Score: 86
$225/night

3 Bdrm Vintage Hideaway Little Italy/ UIC

3 beds
1 bath
6 guests
Average Price:  
$263
14% Cheaper
than normal
AirDNA Score: 86
$99/night

In artistic Pilsen~Continental Breakfast~Near DWTN

2 beds
1 bath
4 guests
Average Price:  
$160
38% Cheaper
than normal
AirDNA Score: 86
$113/night

Bridgeport Garden Apartment

1 bed
1 bath
4 guests
Average Price:  
$104
9% More
than normal
AirDNA Score: 86
$159/night

Private Wicker Park/Bucktown Haven with Yard/Deck

2 beds
1 bath
4 guests
Average Price:  
$197
19% Cheaper
than normal
AirDNA Score: 86
$111/night

Chicago Sunny Classic Private Home Roscoe Village & Wrigley

1 bed
1 bath
3 guests
Average Price:  
$191
42% Cheaper
than normal
AirDNA Score: 86
$80/night

2 Bedrooms- Comfy Chicago Basement disinfected!

2 beds
1 bath
5 guests
Average Price:  
$107
25% Cheaper
than normal
AirDNA Score: 86
$246/night

Charming 2BR on Quiet Street Close to the Action

2 beds
1 bath
6 guests
Average Price:  
$272
10% Cheaper
than normal
AirDNA Score: 86
$262/night

Chic Decor (No Chores / No Cleaning Fees)

3 beds
1 bath
6 guests
Average Price:  
$319
18% Cheaper
than normal
AirDNA Score: 86
$151/night

Samson’s Place! Uptown: Near Beach w/Free Parking

2 beds
1 bath
4 guests
Average Price:  
$226
33% 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
$175/night

⭐FAB LOCATION next to DOWNTOWN! Laundry, parking ⭐

2 beds
1 bath
7 guests
Average Price:  
$225
22% Cheaper
than normal
AirDNA Score: 86
$218/night

Peaceful River West Apt - free gated parking

2 beds
1 bath
4 guests
Average Price:  
$275
21% Cheaper
than normal
AirDNA Score: 86
$110/night

Bright & Spacious Noble Square Loft

1 bed
1 bath
4 guests
Average Price:  
$173
36% Cheaper
than normal
AirDNA Score: 86
$280/night

Amadeus Stay - Hip Central 3bdrm Apt +Free Parking

3 beds
1 bath
5 guests
Average Price:  
$354
21% Cheaper
than normal
AirDNA Score: 86
$977/night

Come Together in This Vibrant Restored Mansion near Wrigley

9 beds
3.5 baths
16 guests
Average Price:  
$1144
15% Cheaper
than normal
AirDNA Score: 86
$195/night

Trendy Living in Chicago''s Coolest Airbnb Art Gallery Condo

3 beds
2 baths
8 guests
Average Price:  
$288
32% Cheaper
than normal
AirDNA Score: 86
$151/night

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

3 beds
1.5 baths
6 guests
Average Price:  
$212
29% Cheaper
than normal
AirDNA Score: 86
$205/night

King Bed, 3BD, Fast WIFI, 4K TV | 5 Min to Airport

3 beds
2 baths
6 guests
Average Price:  
$236
13% Cheaper
than normal
AirDNA Score: 86
$119/night

Sydni Suites near the University of Chicago 2-bdrm

2 beds
1 bath
6 guests
Average Price:  
$166
28% Cheaper
than normal
AirDNA Score: 86
$220/night

Modern Apartment in Wicker Park with Outdoor Space

2 beds
1 bath
6 guests
Average Price:  
$226
3% Cheaper
than normal
AirDNA Score: 86
$323/night

Newly Renovated, Spacious Urban Getaway

3 beds
2 baths
10 guests
Average Price:  
$386
16% Cheaper
than normal
AirDNA Score: 86
$150/night

3BR Work and Family Friendly, Free Parking

3 beds
1 bath
5 guests
Average Price:  
$232
35% Cheaper
than normal
AirDNA Score: 86
$147/night

Redesigned Lower Level Studio in Historic Building

studio
1 bath
4 guests
Average Price:  
$190
23% Cheaper
than normal
AirDNA Score: 85
$130/night

Jean''s House—Restored Historic Andersonville Craftsman

2 beds
1 bath
4 guests
Average Price:  
$216
40% Cheaper
than normal
AirDNA Score: 85
$65/night

Cozy Garden Apartment in lovely Old Irving Park

1 bed
1 bath
1 guest
Average Price:  
$86
24% Cheaper
than normal
AirDNA Score: 85
$399/night

Modern New Built in the Heart of City

3 beds
2 baths
8 guests
Average Price:  
$416
4% Cheaper
than normal
AirDNA Score: 85
$291/night

Comfy River West Apt with Free Gated Parking

2 beds
1 bath
4 guests
Average Price:  
$256
14% More
than normal
AirDNA Score: 85
$135/night

Cozy Andersonville Cabin

1 bed
1 bath
4 guests
Average Price:  
$173
22% Cheaper
than normal
AirDNA Score: 85
$120/night

The Lodge Chicago

1 bed
1 bath
3 guests
Average Price:  
$152
21% Cheaper
than normal
AirDNA Score: 85
$99/night

Stylish mid-century modern apartment

1 bed
1 bath
2 guests
Average Price:  
$74
34% More
than normal
AirDNA Score: 84
$165/night

Stylish Studio in Historic Logan Square

1 bed
1 bath
2 guests
Average Price:  
$144
15% More
than normal
AirDNA Score: 84
$120/night

Sunny, Cozy, Colorful Andersonville

2 beds
1 bath
4 guests
Average Price:  
$157
24% Cheaper
than normal
AirDNA Score: 82
$103/night

Sunny and Funky Logan Square Garden Apartment

1 bed
1 bath
2 guests
Average Price:  
$104
1% Cheaper
than normal
AirDNA Score: 81
$999/night

3BD, 2BA Hotel Suite -Fireplace

3 beds
2 baths
7 guests
Average Price:  
$635
57% More
than normal
AirDNA Score: 80
$139/night

BERNARD CHATEAU - LOGAN SQUARE

3 beds
1 bath
6 guests
Average Price:  
$179
22% Cheaper
than normal
AirDNA Score: 80
$600/night

Beautiful Modern, large, 4BR/4BA Private Home

4 beds
4.5 baths
16 guests
Average Price:  
$679
12% Cheaper
than normal
AirDNA Score: 79
$239/night

Duplex 4BR Roomy Logan Square on Tree Lined Street

4 beds
2 baths
10 guests
Average Price:  
$283
16% Cheaper
than normal
AirDNA Score: 79
$116/night

Soaring Lake Views from Corner 2br/2ba in Downtown

2 beds
2 baths
6 guests
Average Price:  
$321
64% 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
$70/night

Avondale Oasis Floor 3

studio
1 bath
2 guests
Average Price:  
$135
48% Cheaper
than normal
AirDNA Score: 79
$2473/night

Rock and Roll Paradise

4 beds
3.5 baths
14 guests
Average Price:  
$2691
8% Cheaper
than normal
AirDNA Score: 79
$275/night

Centrally located Apartment near Fulton Market

1 bed
1 bath
4 guests
Average Price:  
$313
12% Cheaper
than normal
AirDNA Score: 79
$85/night

Ravenswood Guest House Annex

1 bed
1 bath
4 guests
Average Price:  
$102
17% Cheaper
than normal
AirDNA Score: 79
$189/night

Tastefully designed 1500 Sq of Homeyness!

2 beds
2 baths
6 guests
Average Price:  
$207
9% Cheaper
than normal
AirDNA Score: 79
$154/night

PerfectLocationDowntown ApartmentGreatView monthly

1 bed
1 bath
3 guests
Average Price:  
$142
8% More
than normal
AirDNA Score: 79
$176/night

Lovely 1BR Apt Steps from Wrigley!

1 bed
1 bath
4 guests
Average Price:  
$181
3% Cheaper
than normal
AirDNA Score: 79
$250/night

Garden Apartment in Historic Hyde Park Mansion

2 beds
2 baths
5 guests
Average Price:  
$232
8% More
than normal
AirDNA Score: 79
$119/night

Sydni Suites near the UChicago Campus

2 beds
1 bath
6 guests
Average Price:  
$136
12% Cheaper
than normal
AirDNA Score: 79
$97/night

Historic East Village in West Town

1 bed
1 bath
4 guests
Average Price:  
$105
8% Cheaper
than normal
AirDNA Score: 79
$110/night

Contemporary 2 bedroom south facing balcony 3

2 beds
1 bath
6 guests
Average Price:  
$139
21% Cheaper
than normal
AirDNA Score: 79
$137/night

The Noble Farmhouse, Sunlit with Private Garden in West Town

2 beds
1 bath
3 guests
Average Price:  
$204
33% Cheaper
than normal
AirDNA Score: 79
$107/night

Cozy Ukrainian Village Two Bedroom Apartment

2 beds
1 bath
4 guests
Average Price:  
$147
27% Cheaper
than normal
AirDNA Score: 79
$277/night

Spacious Holiday Getaway for Family & Friends

3 beds
1 bath
6 guests
Average Price:  
$360
23% Cheaper
than normal
AirDNA Score: 79
$95/night

Perfect location in Lincoln Park—free parking spot

1 bed
1 bath
3 guests
Average Price:  
$113
16% Cheaper
than normal
AirDNA Score: 79
$118/night

Private apartment inside house GATED FREE Parking

1 bed
1 bath
2 guests
Average Price:  
$186
37% Cheaper
than normal
AirDNA Score: 79
$114/night

Sydni Suites near the University of Chgo 2-bdrm.

2 beds
1 bath
6 guests
Average Price:  
$141
19% Cheaper
than normal
AirDNA Score: 79
$240/night

City Hideaway

2 beds
1 bath
3 guests
Average Price:  
$268
10% Cheaper
than normal
AirDNA Score: 79
$109/night

Sawyer Get-Away in Logan Square

2 beds
1 bath
4 guests
Average Price:  
$150
27% Cheaper
than normal
AirDNA Score: 79
$149/night

River North''s Finest - Covid Safer - Monthly Only

2 beds
2 baths
6 guests
Average Price:  
$149
0% Cheaper
than normal
AirDNA Score: 79
$75/night

Cortez House - 2BR - Free Parking - Great Beds

2 beds
1 bath
4 guests
Average Price:  
$166
55% Cheaper
than normal
AirDNA Score: 79
$145/night

Private, Charming, Coach House Loft in Andersonville

studio
1 bath
2 guests
Average Price:  
$160
9% Cheaper
than normal
AirDNA Score: 79
$125/night

Charming renovated Victorian apartment in Old Town

1 bed
1 bath
2 guests
Average Price:  
$125
0% Cheaper
than normal
AirDNA Score: 79
$400/night

Pro Cleaned, Lakeview Greystone One Block from Wrigley Field

5 beds
2 baths
10 guests
Average Price:  
$389
3% More
than normal
AirDNA Score: 79
$130/night

Modern Logan Square Apartment near Public Transit

2 beds
1 bath
4 guests
Average Price:  
$138
6% Cheaper
than normal
AirDNA Score: 79
$799/night

The Hamlin In Logan Square 4BR/2BA w/Parking!

4 beds
2 baths
12 guests
Average Price:  
$716
12% More
than normal
AirDNA Score: 79
$119/night

Chicago Charm Abounds at the Ivy-Covered Coach House

1 bed
1 bath
3 guests
Average Price:  
$195
39% Cheaper
than normal
AirDNA Score: 79
$118/night

Convenient Hyde Park 2 Bedroom Apartment

2 beds
1 bath
4 guests
Average Price:  
$129
9% Cheaper
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
$114/night

Spacious and Welcoming Ravenswood Garden Unit

1 bed
1 bath
4 guests
Average Price:  
$130
12% Cheaper
than normal
AirDNA Score: 79
$297/night

Convenient Brand New 3 Bedroom Apartment w/WIFI

3 beds
2 baths
8 guests
Average Price:  
$236
26% More
than normal
AirDNA Score: 79
$225/night

Beautiful & Inspiring Three Bedroom Home in Roscoe Village

3 beds
1 bath
5 guests
Average Price:  
$211
7% More
than normal
AirDNA Score: 79
$93/night

⚡️NEW! Stylish & Cozy 3BDRM, 10min/ORD, 20min/DT❤️

3 beds
1 bath
6 guests
Average Price:  
$139
33% Cheaper
than normal
AirDNA Score: 79
$99/night

Spacious 1BR apartment in a central location

1 bed
1 bath
3 guests
Average Price:  
$92
8% More
than normal
AirDNA Score: 79
$363/night

Cannabis Condo 4BR

4 beds
1 bath
8 guests
Average Price:  
$355
2% More
than normal
AirDNA Score: 79
$136/night

Spacious & Sunny 1 BDR filled w/ plants - Logan SQ

1 bed
1 bath
2 guests
Average Price:  
$152
11% Cheaper
than normal
AirDNA Score: 79
$111/night

Augusta''s Garden | Noble Square | Wicker Park

studio
1 bath
3 guests
Average Price:  
$189
41% Cheaper
than normal
AirDNA Score: 79
$86/night

Logan Square Video Game Loft

studio
1 bath
4 guests
Average Price:  
$130
34% Cheaper
than normal
AirDNA Score: 79
$125/night

Comfortable Home Base, Close to Everything!

2 beds
1 bath
4 guests
Average Price:  
$231
46% Cheaper
than normal
AirDNA Score: 79
$109/night

Andersonville Cozy 1 bedroom basement suite

1 bed
1 bath
2 guests
Average Price:  
$131
17% Cheaper
than normal
AirDNA Score: 79
$104/night

Lovely Near Loyola - Enjoy the Wonderful Sun Room

3 beds
2 baths
7 guests
Average Price:  
$190
45% Cheaper
than normal
AirDNA Score: 79
$450/night

The Roscoe House near Wrigley Field

3 beds
3 baths
8 guests
Average Price:  
$482
7% Cheaper
than normal
AirDNA Score: 79
$88/night

Private suite in Lincoln Square

1 bed
1 bath
4 guests
Average Price:  
$115
23% Cheaper
than normal
AirDNA Score: 79
$99/night

Amazing 2 bedroom apartment on prime location

2 beds
1 bath
4 guests
Average Price:  
$115
14% Cheaper
than normal
AirDNA Score: 79
$128/night

"Home Away from Home" - Free Street Parking!

2 beds
1 bath
6 guests
Average Price:  
$145
12% Cheaper
than normal
AirDNA Score: 79
$99/night

Greystone Haven in Logan Square

2 beds
2 baths
5 guests
Average Price:  
$205
52% Cheaper
than normal
AirDNA Score: 79
$600/night

“Wrigleyville” 75 yards from Wrigley Field

2 beds
1 bath
12 guests
Average Price:  
$413
45% More
than normal
AirDNA Score: 79
$98/night

⚡️NEW! Modern & Spacious, 10min to ORD, 20 to DT❤️

1 bed
1 bath
2 guests
Average Price:  
$128
23% Cheaper
than normal
AirDNA Score: 79
$125/night

Bright, Cheery Logan Square Getaway

1 bed
1 bath
6 guests
Average Price:  
$162
23% Cheaper
than normal
AirDNA Score: 78
$227/night

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

2 beds
1 bath
6 guests
Average Price:  
$226
0% Cheaper
than normal
AirDNA Score: 78
$115/night

iKlektik House // Cardinal

1 bed
1 bath
4 guests
Average Price:  
$136
15% Cheaper
than normal
AirDNA Score: 78
$85/night

Spacious & Private Loft Apt in Historic Beverly

1 bed
1 bath
2 guests
Average Price:  
$90
6% Cheaper
than normal
AirDNA Score: 78
$235/night

Soaring 2br/2ba SkyTerrace + Deck!

2 beds
2 baths
6 guests
Average Price:  
$350
33% Cheaper
than normal
AirDNA Score: 78
$225/night

Long Stays, Highly Rated

2 beds
2 baths
4 guests
Average Price:  
$222
1% More
than normal