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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 , 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  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 , 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  right now, why wait?

Crestwood Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$454

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 hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.4/10 Very Good! (5,333 reviews)
The location is great! We had to leave a couple hours into our stay due to a major snowstorm so my feedback is limited. We weren’t able to enjoy the breakfast this time but it was fantastic last time we were there. The room was very clean and staff were extremely helpful. I received a text asking ...

Reviewed on Nov 30, 2025

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 ...
8.8/10 Excellent! (3,421 reviews)
We enjoyed our stay at Hilton Magnificent Chicago, definitely we will return to this beautiful , clean and nice place. I just have a recommendation, I like to have more light at the room, for me was so dark, not enough artificial light.

Reviewed on Dec 2, 2025

Hilton Chicago/Magnificent Mile Suites
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (2,121 reviews)
W

Reviewed on Dec 2, 2025

Palmer House a Hilton Hotel
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! (9,698 reviews)
Perfect location

Reviewed on Dec 2, 2025

Congress Plaza Hotel
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Book a stay at this 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! (1,946 reviews)
The staff were so kind and helpful, from directions to sharing places to eat, they were brilliant! Plus, it is close to every thing!

Reviewed on Nov 29, 2025

Club Quarters Hotel Wacker at Michigan, Chicago
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place Chicago IL
Book a stay at this 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! (4,092 reviews)
Everything was Amazing

Reviewed on Nov 28, 2025

citizenM Chicago Downtown
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
9.2/10 Wonderful! (3,097 reviews)
Clean hotel and room! All employees were so nice and helpful. Check in was a breeze. The guys out front so nice and helpful. Great location less than 10 minutes from so many things. Will definitely be staying here again.

Reviewed on Dec 2, 2025

The Royal Sonesta Chicago Downtown
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
Book a stay at this 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! (1,733 reviews)
Courteous staff Clean room

Reviewed on Dec 2, 2025

Crowne Plaza Chicago West Loop by IHG
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.