Search Cheap Flights to
Crestwood

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Crestwood Flights as Low as $72

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

Frontier Airlines
Frontier Airlines
Frontier Airlines
Spirit Airlines
Frontier Airlines
Bargain Flight
American Airlines
Delta
Bargain Flight
Frontier Airlines
American Airlines
Delta
American Airlines
American Airlines
Delta
American Airlines

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 14 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 $72, 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 $72 right now, why wait?

Crestwood Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$72

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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,001 reviews)
Rooms were in far condition but poorly maintained.

Reviewed on Mar 23, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,612 reviews)
Amazing service, staff were very attentive and friendly! Buffet selection was top tier.

Reviewed on Mar 23, 2026

Hotel Riu Plaza Chicago
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 hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,779 reviews)
Breakfast fresh. Pool was finr

Reviewed on Mar 23, 2026

Embassy Suites by Hilton Chicago Downtown River North
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 ...
9/10 Wonderful! (3,970 reviews)
Everything was great. All the staff was friendly, clean rooms and hotel as a whole. The only complaint was that since it was nice out for a spring day, the room was hotter than expected.

Reviewed on Mar 23, 2026

Hilton Chicago/Magnificent Mile Suites
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,154 reviews)
Yes

Reviewed on Mar 23, 2026

Aloft Chicago Mag Mile
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 breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,756 reviews)
The entire hotel was a 10/10. Would definitely recommend. Also the bartender KERRY in the restaurant of the hotel was perfect, very nice, personable, and made our stay even better!!!

Reviewed on Mar 23, 2026

The Wade
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,463 reviews)
So so

Reviewed on Mar 23, 2026

Hyatt Regency Chicago
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the ...
9/10 Wonderful! (3,236 reviews)
Absolutely not satisfied with my stay within one hour of being there and paying for Valet my truck was damaged in the process of them parking it and they are not trying to take any accountability for it. I walked down and the valet attendant that had parked my car apparently had left for the night… ...

Reviewed on Mar 23, 2026

Swissotel - Chicago
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.