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Over 1,000 places in Chicago

Boutique hotel in Chicago

Luxury Stay - Claridge House, Queen Room

1 queen bed

Apr 28 – May 3

$106 per night

4.43 out of 5 average rating, 689 reviews

Superhost

Apartment in Chicago

Chic Furnished Studio w/ Laundry

1 queen bed

Apr 28 – May 3

$67 per night, originally $98

4.79 out of 5 average rating, 108 reviews

Apartment in Chicago

Standard King Bed Hotel Room at Magnificent Mile

1 king bed

Apr 28 – May 3

$102 per night

4.58 out of 5 average rating, 108 reviews

Superhost

Apartment in Chicago

Decorated 1BR Apt, Natural Light, Comfy King Beds

1 king bed

Apr 21 – 26

$67 per night, originally $104

4.8 out of 5 average rating, 208 reviews

Superhost

Apartment in Chicago

1BR Getaway Apt Vintage Modern in Lincoln Square

1 queen bed

Apr 21 – 26

$67 per night, originally $92

4.79 out of 5 average rating, 156 reviews

Superhost

Apartment in Chicago

Modern 2BR Apt with Cozy Interior at Logan Square

2 queen beds

Apr 21 – 26

$68 per night, originally $111

4.86 out of 5 average rating, 143 reviews

Apartment in Chicago

Standard Double Hotel Room at Magnificent Mile

2 double beds

Apr 28 – May 3

$102 per night

4.75 out of 5 average rating, 155 reviews

Guest favorite

Tiny home in Burr Ridge

Less is more! Pet friendly Tiny Home near Chicago!

2 beds

Jun 2 – 7

$105 per night

4.92 out of 5 average rating, 238 reviews

Apartment in Chicago

The Elstonian

3 queen beds

Apr 28 – May 3

$150 per night

New place to stay

Superhost

Apartment in Chicago

Adorable 1BR Apartment w/ In-unit Laundry

1 queen bed

Apr 28 – May 3

$79 per night, originally $113

4.94 out of 5 average rating, 81 reviews

Apartment in Chicago

Kasa | Enjoy City Views on Your Balcony | Chicago

1 queen bed

Apr 21 – 26

$169 per night

4.84 out of 5 average rating, 416 reviews

Apartment in Chicago

Sentral Premium 2BR Apt South Loop Chicago

2 queen beds

Apr 21 – 26

$256 per night, originally $350

4.62 out of 5 average rating, 234 reviews

Guest favorite

Condo in Chicago

Lincoln Park Hideaway - 5 Min Walk to the Park!

3 beds

Apr 21 – 26

$110 per night, originally $155

4.92 out of 5 average rating, 101 reviews

Guest favorite

Home in Chicago

Charming 3-BED in Lincoln Park/ Old Town & Parking

3 beds

Apr 28 – May 3

$150 per night, originally $188

5.0 out of 5 average rating, 44 reviews

Guest favorite

Condo in Chicago

Lincoln Square Gem!

2 queen beds

Sep 15 – 20

$132 per night

4.98 out of 5 average rating, 328 reviews

Guest favorite

Guest suite in Chicago

Cozy one-bedroom suite in the heart of West Loop

1 double bed

May 11 – 16

$155 per night

4.91 out of 5 average rating, 80 reviews

Apartment in Chicago

VintageLoversEscape|Homey|Stylish1BR|CloseToBeach

1 bed

Apr 19 – 24

$80 per night

4.8 out of 5 average rating, 40 reviews

Guest favorite

Apartment in Chicago

Garden Unit Getaway.

1 queen bed

Apr 21 – 26

$125 per night, originally $160

4.95 out of 5 average rating, 66 reviews