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Crestwood

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Crestwood Flights as Low as $110

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

Frontier Airlines
Sat, May 24 - Sun, May 25
DEN
Denver Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 4 hours ago
$110
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Denver Intl. to O'Hare Intl., returning Sun, May 25, priced at $110 found 4 hours ago
Frontier Airlines
Wed, May 14 - Wed, May 21
IAH
George Bush Intercontinental
MDW
Midway Intl.
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 14 from George Bush Intercontinental to Midway Intl., returning Wed, May 21, priced at $115 just found
United
Sat, May 24 - Sat, May 31
DEN
Denver Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 4 hours ago
$127
Roundtrip
found 4 hours ago
Select United flight, departing Sat, May 24 from Denver Intl. to O'Hare Intl., returning Sat, May 31, priced at $127 found 4 hours ago
Spirit Airlines
Thu, May 15 - Tue, May 20
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$133 Roundtrip, found 1 hour ago
$133
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 15 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 20, priced at $133 found 1 hour ago
Spirit Airlines
Thu, May 8 - Tue, May 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$135 Roundtrip, just found
$135
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 8 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 13, priced at $135 just found
Frontier Airlines
Sat, May 24 - Thu, May 29
DEN
Denver Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 5 days ago
$135
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 24 from Denver Intl. to O'Hare Intl., returning Thu, May 29, priced at $135 found 5 days ago
Frontier Airlines
Sat, May 24 - Fri, May 30
DEN
Denver Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 24 from Denver Intl. to O'Hare Intl., returning Fri, May 30, priced at $140 found 5 days ago
Spirit Airlines
Thu, May 8 - Tue, May 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$141 Roundtrip, just found
$141
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 8 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 13, priced at $141 just found
United
Sat, May 24 - Sun, May 25
DEN
Denver Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 4 hours ago
$154
Roundtrip
found 4 hours ago
Select United flight, departing Sat, May 24 from Denver Intl. to O'Hare Intl., returning Sun, May 25, priced at $154 found 4 hours ago
American Airlines
Sat, May 24 - Sun, May 25
DEN
Denver Intl.
ORD
O'Hare Intl.
$180 Roundtrip, found 4 hours ago
$180
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, May 24 from Denver Intl. to O'Hare Intl., returning Sun, May 25, priced at $180 found 4 hours ago
United
Wed, Apr 30 - Wed, May 7
GRB
Austin Straubel Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 1 hour ago
$203
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Apr 30 from Austin Straubel Intl. to O'Hare Intl., returning Wed, May 7, priced at $203 found 1 hour ago
Delta
Sat, Jun 21 - Sat, Jun 21
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$211 Roundtrip, found 1 hour ago
$211
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Jun 21 from George Bush Intercontinental to O'Hare Intl., returning Sat, Jun 21, priced at $211 found 1 hour ago
Frontier Airlines
Tue, Apr 22 - Tue, Apr 22
DEN
Denver Intl.
MDW
Midway Intl.
$399 Roundtrip, found 4 hours ago
$399
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Apr 22 from Denver Intl. to Midway Intl., returning Tue, Apr 22, priced at $399 found 4 hours ago
JetBlue Airways
Mon, May 5 - Fri, May 9
DEN
Denver Intl.
ORD
O'Hare Intl.
$436 Roundtrip, found 4 hours ago
$436
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Mon, May 5 from Denver Intl. to O'Hare Intl., returning Fri, May 9, priced at $436 found 4 hours ago
United
Thu, May 8 - Fri, May 16
ANC
Ted Stevens Anchorage Intl.
ORD
O'Hare Intl.
$437 Roundtrip, found 1 hour ago
$437
Roundtrip
found 1 hour ago
Select United flight, departing Thu, May 8 from Ted Stevens Anchorage Intl. to O'Hare Intl., returning Fri, May 16, priced at $437 found 1 hour ago
Alaska Airlines
Wed, May 14 - Sat, May 17
ANC
Ted Stevens Anchorage Intl.
ORD
O'Hare Intl.
$505 Roundtrip, found 1 hour ago
$505
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Wed, May 14 from Ted Stevens Anchorage Intl. to O'Hare Intl., returning Sat, May 17, priced at $505 found 1 hour 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 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 $110, 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 $110 right now, why wait?

Crestwood Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$85

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 $175 per night from Apr 20 to Apr 21
$175
includes taxes & fees
Apr 20 - Apr 21
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! (3,882 reviews)
"Overall good hotel. Breakfast was good, the buffet food was okay but the made to order line was worth waiting in. Wait for the elevators was a bit long but hotel was busy on a weekend. Bed was not the most comfortable but pillows were great. One bedroom suite was spacious. Located in a busy downtown ..."

Reviewed on Apr 15, 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $241 per night from Apr 18 to Apr 19
$241
includes taxes & fees
Apr 18 - Apr 19
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! (2,053 reviews)
"Nice hotel! Still feels hip. Great views. Great location. Clean! Just starting to show some wear but clean."

Reviewed on Apr 15, 2025

Swissotel - Chicago
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 $139 per night from Apr 21 to Apr 22
$139
includes taxes & fees
Apr 21 - Apr 22
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! (1,009 reviews)
"From the very time that I walked through the door the staff was very polite and informative. The property was beautiful and the location was excellent. My family and I enjoyed our first trip to Chicago."

Reviewed on Apr 16, 2025

Crowne Plaza Chicago West Loop by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $139 per night from Apr 21 to Apr 22
$139
includes taxes & fees
Apr 21 - Apr 22
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! (2,135 reviews)
"Room was really spacious!"

Reviewed on Apr 16, 2025

Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $147 per night from Apr 20 to Apr 21
$147
includes taxes & fees
Apr 20 - Apr 21
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! (8,676 reviews)
My favorite
"I’ve stayed here many times throughout the years. Beautiful view of Buckingham fountain. Short walk to Osaka Sushi for an Udon noodle bowl. We will walk to the Contemporary Museum of Art today. Just a joyous stay at Congress Plaza"

Reviewed on Apr 16, 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $144 per night from Apr 23 to Apr 24
$144
includes taxes & fees
Apr 23 - Apr 24
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! (4,061 reviews)
"Great location for most things being no more than a 15 minute walk or bus ride."

Reviewed on Apr 16, 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 $219 per night from Apr 20 to Apr 21
$219
includes taxes & fees
Apr 20 - Apr 21
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! (1,641 reviews)
"The hotel was beautiful and clean. The art deco design gave us a sense of place in Chicago. It’s always fun to feel like a hotel represents its location well and the Allegro does. It was a great location to access anywhere you wanted to go in Chicago. The most impressive part was the hospitality ..."

Reviewed on Apr 15, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $136 per night from Apr 20 to Apr 21
$136
includes taxes & fees
Apr 20 - Apr 21
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! (2,928 reviews)
"Such a beautiful hotel, very clean and very modern. Beds are alittle stuff but loved how everything was controlled by the ipad. Smaller rooms but more minimalist style"

Reviewed on Apr 15, 2025

citizenM Chicago Downtown
See all 3,363 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.