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Crestwood

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Crestwood Flights as Low as $76

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Jul 8 - Tue, Jul 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, just found
$76
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jul 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $76 just found
Spirit Airlines
Tue, Jul 15 - Tue, Jul 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 4 hours ago
$88
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Jul 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $88 found 4 hours ago
Spirit Airlines
Tue, Jul 8 - Fri, Jul 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 4 hours ago
$97
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $97 found 4 hours ago
Spirit Airlines
Wed, Jul 9 - Mon, Jul 14
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 12 hours ago
$98
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Wed, Jul 9 from Harry Reid Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $98 found 12 hours ago
Frontier Airlines
Tue, Aug 5 - Wed, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$108 Roundtrip, found 11 hours ago
$108
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Aug 6, priced at $108 found 11 hours ago
United
Tue, Aug 19 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 hour ago
$132
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $132 found 1 hour ago
Delta
Tue, Aug 19 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 hour ago
$132
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $132 found 1 hour ago
American Airlines
Tue, Aug 19 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 hour ago
$132
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $132 found 1 hour ago
Spirit Airlines
Tue, Jul 8 - Tue, Jul 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 3 hours ago
$137
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 8, priced at $137 found 3 hours ago
Frontier Airlines
Fri, Jun 27 - Mon, Jun 30
LAS
Harry Reid Intl.
MDW
Midway Intl.
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jun 27 from Harry Reid Intl. to Midway Intl., returning Mon, Jun 30, priced at $172 found 1 day ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 1 hour ago
$191
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 found 1 hour ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 12 hours ago
$197
Roundtrip
found 12 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 12 hours ago
Alaska Airlines
Tue, Jul 22 - Tue, Jul 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$236 Roundtrip, found 12 hours ago
$236
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Tue, Jul 22 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $236 found 12 hours ago
Delta
Mon, Aug 11 - Tue, Aug 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$256 Roundtrip, found 1 hour ago
$256
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Aug 11 from Los Angeles Intl. to Midway Intl., returning Tue, Aug 12, priced at $256 found 1 hour ago
JetBlue Airways
Thu, Sep 4 - Mon, Sep 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$329 Roundtrip, just found
$329
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Sep 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $329 just found
Sun Country Airlines
Sun, Jul 13 - Mon, Jul 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$343 Roundtrip, found 9 hours ago
$343
Roundtrip
found 9 hours ago
Select Sun Country Airlines flight, departing Sun, Jul 13 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $343 found 9 hours ago

Cheap Flights to Crestwood

Fall in love at first flight with your vacation to Crestwood by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Crestwood on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Crestwood, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Crestwood

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Crestwood with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Crestwood?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Crestwood are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Crestwood?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Crestwood.

What airport is best to fly into Crestwood?

When you’re planning your trip to Crestwood, convenience is the name of the game. Luckily, Crestwood Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Crestwood must-do list.

How much are flights to Crestwood?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Crestwood on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $76, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Crestwood?

The trick to saving a stack of cash on your flight to Crestwood? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $76 right now, why wait?

Crestwood Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$75

Last Minute Hotel Deals in Crestwood

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,198 reviews)
"This was a really nice location. It was walkable and close to subway."

Reviewed on Jun 11, 2025

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Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (1,863 reviews)
"Great hotel. Location cost to downtown, the Pier, and a lot of restaurants and night life. Property and rooms are in great shape. Staff is very friendly and helpful."

Reviewed on Jun 8, 2025

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InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,294 reviews)
"Very nice"

Reviewed on Jun 10, 2025

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Hilton Chicago/Magnificent Mile Suites
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,166 reviews)
"The location is wonderful, the bar/restaurant area was very good. Food and pricing well worth it. The outdoor terrace was my highlight. Room super cute and clean, Loved the remote shades. A few downsides, need 24 hour notice for a room cleaning. (I did not pay attention to the details, but was accommodated ..."

Reviewed on Jun 11, 2025

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citizenM Chicago Downtown
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,872 reviews)
"Excellent place."

Reviewed on Jun 10, 2025

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Congress Plaza Hotel
The Wade
The Wade
4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Book a stay at this luxury hotel in Chicago. Enjoy room service, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
8/10 Very Good! (1,015 reviews)
"Love it."

Reviewed on Jun 10, 2025

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The Wade
Freehand Chicago
Freehand Chicago
4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (1,919 reviews)
"Nice place, good staff, fun place."

Reviewed on Jun 10, 2025

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Freehand Chicago
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
8.8/10 Excellent! (2,214 reviews)
"Great location, right on the river and three blocks from Michigan Ave and two blocks from the the Big Shiny Bean. Exfellent service, great vuews from our room and really enjoyed the burger and hash browns at the Palms restaurant in the main lobby."

Reviewed on Jun 9, 2025

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Swissotel - Chicago
See all 3,532 properties in Crestwood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.