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Crestwood

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Crestwood Flights as Low as $82

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

Spirit Airlines
Tue, May 13 - Tue, May 13
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$82 Roundtrip, found 9 hours ago
$82
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Tue, May 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, May 13, priced at $82 found 9 hours ago
Spirit Airlines
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$96 Roundtrip, found 6 days ago
$96
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, May 20 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $96 found 6 days ago
Spirit Airlines
Wed, Jun 11 - Wed, Jul 2
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$102 Roundtrip, found 1 hour ago
$102
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Jun 11 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Jul 2, priced at $102 found 1 hour ago
Spirit Airlines
Tue, May 13 - Sat, May 24
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$103 Roundtrip, found 13 hours ago
$103
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Tue, May 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, May 24, priced at $103 found 13 hours ago
Spirit Airlines
Tue, May 27 - Mon, Jun 2
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$104 Roundtrip, found 16 hours ago
$104
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Tue, May 27 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Jun 2, priced at $104 found 16 hours ago
Frontier Airlines
Sun, May 25 - Thu, Jun 5
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 17 hours ago
$124
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sun, May 25 from Raleigh - Durham Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $124 found 17 hours ago
United
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Select United flight, departing Tue, May 20 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $157 found 6 days ago
American Airlines
Wed, Jul 9 - Wed, Jul 23
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jul 9 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Jul 23, priced at $159 found 3 days ago
Frontier Airlines
Mon, Jun 9 - Thu, Jun 12
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Philadelphia Intl. to O'Hare Intl., returning Thu, Jun 12, priced at $167 found 4 days ago
Bargain Flight
Wed, May 28 - Thu, Jun 5
BUF
Buffalo Niagara Intl.
ORD
O'Hare Intl.
$170 Roundtrip, found 14 hours ago
$170
Roundtrip
found 14 hours ago
Select Bargain Flight flight, departing Wed, May 28 from Buffalo Niagara Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $170 found 14 hours ago
Delta
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, May 20 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $177 found 6 days ago
JetBlue Airways
Tue, May 13 - Wed, May 21
BUF
Buffalo Niagara Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, May 13 from Buffalo Niagara Intl. to O'Hare Intl., returning Wed, May 21, priced at $183 found 1 day ago
Delta
Sat, May 24 - Wed, May 28
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 24 from Raleigh - Durham Intl. to Midway Intl., returning Wed, May 28, priced at $200 found 1 day ago
Frontier Airlines
Sun, May 11 - Thu, May 15
BUF
Buffalo Niagara Intl.
MDW
Midway Intl.
$200 Roundtrip, found 17 hours ago
$200
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sun, May 11 from Buffalo Niagara Intl. to Midway Intl., returning Thu, May 15, priced at $200 found 17 hours ago
Frontier Airlines
Sat, May 17 - Mon, May 19
TTN
Mercer
ORD
O'Hare Intl.
$214 Roundtrip, found 4 days ago
$214
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, May 17 from Mercer to O'Hare Intl., returning Mon, May 19, priced at $214 found 4 days ago
Delta
Sat, May 3 - Sat, May 10
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$411 Roundtrip, found 1 day ago
$411
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 3 from Newark Liberty Intl. Airport to Midway Intl., returning Sat, May 10, priced at $411 found 1 day 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 May, 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 15 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 $82, 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 $82 right now, why wait?

Crestwood Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$82

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
The price is $189 per night from May 11 to May 12
$189
includes taxes & fees
May 11 - May 12
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. ...
8.2/10 Very Good! (3,954 reviews)
"Excellent location and very clean. Traveled solo with 2 kids and felt safe. Valet parking option needs better signage. Would absolutely stay here again."

Reviewed on Apr 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $189 per night from May 27 to May 28
$189
includes taxes & fees
May 27 - May 28
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! (8,729 reviews)
"Amazing stay and people"

Reviewed on Apr 28, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $181 per night from May 11 to May 12
$181
includes taxes & fees
May 11 - May 12
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! (2,167 reviews)
"Everything excellent just in our room we struggled with hot water… but everything ok"

Reviewed on Apr 28, 2025

Hilton Chicago/Magnificent Mile Suites
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $235 per night from May 2 to May 3
$235
includes taxes & fees
May 2 - May 3
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 ...
"Great Customer Service! Great Stay! close to downtown Chicago !"

Reviewed on Apr 27, 2025

Swissotel - Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $164 per night from May 8 to May 9
$164
includes taxes & fees
May 8 - May 9
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (4,101 reviews)
"Thus property was beautiful, very clean, friendly staff and there was free coffee. Amazing views made it even better. We walked across the street to the River Walk and down the block to a boat tour. We also walked to a bar and a restaurant downtown. If we go back to Chicago, we would definitely stay ..."

Reviewed on Apr 27, 2025

River Hotel
The Allegro Royal Sonesta Hotel Chicago Loop
The Allegro Royal Sonesta Hotel Chicago Loop
4 out of 5
171 W Randolph St, Chicago, IL
The price is $232 per night from May 11 to May 12
$232
includes taxes & fees
May 11 - May 12
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
8.8/10 Excellent! (1,672 reviews)
"Lovely old hotel well maintained. Close to so many sights."

Reviewed on Apr 27, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
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
The price is $129 per night from May 26 to May 27
$129
includes taxes & fees
May 26 - May 27
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! (1,021 reviews)
"Great stay."

Reviewed on Apr 28, 2025

Crowne Plaza Chicago West Loop by IHG
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is $254 per night from May 11 to May 12
$254
includes taxes & fees
May 11 - May 12
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
"The staff was friendly and helpful."

Reviewed on Apr 28, 2025

L7 Chicago by LOTTE
See all 3,411 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.