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Crestwood

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Crestwood Flights as Low as $118

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

Spirit Airlines
Fri, Aug 15 - Sat, Aug 23
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, Aug 15 from Harry Reid Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $118 found 2 days ago
Frontier Airlines
Mon, Aug 25 - Sun, Aug 31
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 4 days ago
$120
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Aug 25 from Harry Reid Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $120 found 4 days ago
Frontier Airlines
Sat, Aug 16 - Mon, Aug 18
DEN
Denver Intl.
ORD
O'Hare Intl.
$125 Roundtrip, found 6 days ago
$125
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Denver Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $125 found 6 days ago
Spirit Airlines
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 2 hours ago
$130
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $130 found 2 hours ago
Spirit Airlines
Fri, Oct 3 - Mon, Oct 6
TPA
Tampa Intl.
ORD
O'Hare Intl.
$136 Roundtrip, found 4 days ago
$136
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Oct 3 from Tampa Intl. to O'Hare Intl., returning Mon, Oct 6, priced at $136 found 4 days ago
United
Thu, Sep 11 - Fri, Sep 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select United flight, departing Thu, Sep 11 from Denver Intl. to O'Hare Intl., returning Fri, Sep 19, priced at $137 found 2 days ago
American Airlines
Fri, Aug 15 - Sat, Aug 23
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 2 days ago
$141
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Aug 15 from Harry Reid Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $141 found 2 days ago
Frontier Airlines
Thu, Jul 31 - Thu, Aug 7
TPA
Tampa Intl.
MDW
Midway Intl.
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jul 31 from Tampa Intl. to Midway Intl., returning Thu, Aug 7, priced at $152 found 3 days ago
Frontier Airlines
Fri, Aug 1 - Sat, Aug 2
DEN
Denver Intl.
MDW
Midway Intl.
$156 Roundtrip, found 14 hours ago
$156
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Fri, Aug 1 from Denver Intl. to Midway Intl., returning Sat, Aug 2, priced at $156 found 14 hours ago
Alaska Airlines
Tue, Oct 7 - Wed, Oct 15
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Oct 7 from Harry Reid Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $188 found 3 days ago
Delta
Thu, Nov 27 - Tue, Dec 2
TPA
Tampa Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 27 from Tampa Intl. to O'Hare Intl., returning Tue, Dec 2, priced at $197 found 3 days ago
JetBlue Airways
Tue, Aug 26 - Wed, Sep 3
TPA
Tampa Intl.
ORD
O'Hare Intl.
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Aug 26 from Tampa Intl. to O'Hare Intl., returning Wed, Sep 3, priced at $219 found 2 days ago
Frontier Airlines
Mon, Sep 8 - Fri, Sep 12
LAS
Harry Reid Intl.
MDW
Midway Intl.
$234 Roundtrip, found 11 hours ago
$234
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Sep 8 from Harry Reid Intl. to Midway Intl., returning Fri, Sep 12, priced at $234 found 11 hours ago
Delta
Tue, Sep 2 - Wed, Sep 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 2 from Los Angeles Intl. to Midway Intl., returning Wed, Sep 3, priced at $251 found 1 day ago
Sun Country Airlines
Wed, Oct 15 - Sun, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$343 Roundtrip, found 2 days ago
$343
Roundtrip
found 2 days ago
Select Sun Country Airlines flight, departing Wed, Oct 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $343 found 2 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Jul 24 - Sat, Jul 26
DEN
Denver Intl.
ORD
O'Hare Intl.
$362 Roundtrip, found 2 days ago
$362
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 24 from Denver Intl. to O'Hare Intl., returning Sat, Jul 26, priced at $362 found 2 days 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 August, 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 $118, 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 $118 right now, why wait?

Crestwood Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$118

Last Minute Hotel Deals in Crestwood

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! (8,936 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Get rates
Congress Plaza Hotel
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! (2,012 reviews)
"Perfect"

Reviewed on Jul 10, 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! (2,431 reviews)
"Good experience! Not the best but not bad, a little pricey for the quality and service offered"

Reviewed on Jul 12, 2025

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Hilton Chicago/Magnificent Mile Suites
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,250 reviews)
"Good place to stay"

Reviewed on Jul 13, 2025

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Crowne Plaza Chicago West Loop by IHG
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! (4,416 reviews)
"We had a wonderful stay in Chicago."

Reviewed on Jul 11, 2025

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Embassy Suites by Hilton Chicago Downtown River North
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! (3,338 reviews)
"This hotel and room were gorgeous. There was an iPad lighting system that my daughter loved. The terrace space was gorgeous and comfortable."

Reviewed on Jul 11, 2025

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citizenM Chicago Downtown
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 out of 5
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
8.2/10 Very Good! (3,466 reviews)
"If you’re looking to stay downtown on a budget, this is a good option for you. My only major complaint is with the elevator, which would get really backed up during breakfast and check out times. A couple minor complaints are that the toiletries offered were subpar and the fitness room had run out ..."

Reviewed on Jul 10, 2025

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The Whitehall Hotel, BW Premier Collection
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,856 reviews)
"Very clean and comfortable room."

Reviewed on Jul 12, 2025

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Hotel Felix River North/Magnificent Mile
See all 3,548 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.