We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Start your search

%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing

Display total before taxes

Search results; Over 1,000 places in Crestwood

Guest favourite

Home in Robbins

Comfy Updated 3 Bdrm/2Bth -Near SXU, MVC & MDW

3 beds

20–25 May

$211 SGD per night

4.97 out of 5 average rating, 36 reviews

Guest favourite

Room in Oak Forest

Stay with AnmarieHosting for 4 years,

Cozy Cove on Chestnut

4–9 May

$97 SGD per night

4.96 out of 5 average rating, 194 reviews

Guest favourite

Room in Alsip

Stay with JosephHosting for 7 years,

Safe clean charming close transportation Viva!

21–26 Apr

$103 SGD per night

4.87 out of 5 average rating, 226 reviews

Guest favourite

Room in Blue Island

Stay with Karen SophieInterior design,

Chicago commuter room

21–26 Apr

$118 SGD per night

4.87 out of 5 average rating, 145 reviews

Guest favourite

Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

3 beds

2–7 Jun

$197 SGD per night

4.85 out of 5 average rating, 48 reviews

Guest favourite

Home in Oak Forest

Cheerful three bedroom, 2 full bath in Oak Forest

4 beds

20–25 Apr

$413 SGD per night

4.91 out of 5 average rating, 75 reviews

Guest favourite

Flat in Blue Island

Charming Unique 2 Bdrm Apartment in Victorian Home

3 beds

8–13 Jun

$188 SGD per night

4.93 out of 5 average rating, 262 reviews

Guest favourite

Home in Chicago

Boho Chic Coach House 30Min to downtown W/ Parking

1 queen bed

20–25 Apr

$163 SGD per night

4.92 out of 5 average rating, 85 reviews

Home in Palos Heights

Charming Palos Heights Home

3 beds

10–15 Jul

$271 SGD per night

Guest favourite

Home in Oak Forest

My Prima Karina 4bd 2ba in Chicago Suburbs

6–11 May

$266 SGD per night

4.92 out of 5 average rating, 51 reviews

Guest favourite

Guest suite in Orland Park

Private Guest Suite 2 Cozy Rooms

2 beds

23–28 May

$187 SGD per night

4.99 out of 5 average rating, 71 reviews

Guest favourite

Home in Blue Island

Warm and comfortable inviting Suburban home !

3 queen beds

24–29 Apr

$190 SGD per night

4.81 out of 5 average rating, 170 reviews

Guest favourite

Home in Worth

Worth It! 3 bedroom ranch home

24–29 Jul

$278 SGD per night

4.94 out of 5 average rating, 35 reviews

Flat in Harvey

The Emerald!

2 beds

21–26 Apr

$126 SGD per night, originally $153 SGD

New place to stay

Home in Markham

The Jewell, Clean, comfortable 3 bed/2bath Home.

3 beds

21–26 Apr

$241 SGD per night, originally $308 SGD

4.88 out of 5 average rating, 115 reviews

Home in Blue Island

Retro 5 bed gem in blue island

6 beds

22–27 Apr

$328 SGD per night

New place to stay

Guest favourite

Flat in Homewood

High-End Oasis Close to Fun

3 beds

28 Apr – 3 May

$254 SGD per night, originally $325 SGD

4.84 out of 5 average rating, 19 reviews

Home in Oak Forest

"Weekend At Tiffany's"

3 beds

20–25 Apr

$394 SGD per night, originally $478 SGD

New place to stay