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Crestwood

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Crestwood Flights as Low as $68

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

Frontier Airlines
Tue, Jun 17 - Tue, Jun 24
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$68 Roundtrip, found 5 days ago
$68
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jun 17 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jun 24, priced at $68 found 5 days ago
Frontier Airlines
Wed, Jun 18 - Wed, Jun 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jun 18 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jun 25, priced at $68 found 6 days ago
Frontier Airlines
Tue, Aug 5 - Wed, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $68 found 4 days ago
Spirit Airlines
Tue, Apr 8 - Tue, Apr 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 2 days ago
$72
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Apr 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Apr 8, priced at $72 found 2 days ago
Spirit Airlines
Thu, Apr 3 - Mon, Apr 7
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Apr 3 from George Bush Intercontinental to O'Hare Intl., returning Mon, Apr 7, priced at $98 found 3 days ago
Frontier Airlines
Wed, Jun 11 - Wed, Jun 18
IAH
George Bush Intercontinental
MDW
Midway Intl.
$104 Roundtrip, found 6 days ago
$104
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jun 11 from George Bush Intercontinental to Midway Intl., returning Wed, Jun 18, priced at $104 found 6 days ago
Frontier Airlines
Tue, Apr 15 - Thu, Apr 24
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$106 Roundtrip, found 5 days ago
$106
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Apr 15 from Dallas-Fort Worth Intl. to Midway Intl., returning Thu, Apr 24, priced at $106 found 5 days ago
United
Fri, Apr 11 - Sun, Apr 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 3 hours ago
$147
Roundtrip
found 3 hours ago
Select United flight, departing Fri, Apr 11 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Apr 13, priced at $147 found 3 hours ago
American Airlines
Fri, Apr 11 - Sun, Apr 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 3 hours ago
$147
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Fri, Apr 11 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Apr 13, priced at $147 found 3 hours ago
American Airlines
Wed, Jul 2 - Sat, Jul 5
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Jul 2 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sat, Jul 5, priced at $159 found 6 days ago
Frontier Airlines
Wed, Apr 2 - Mon, Apr 7
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$180 Roundtrip, found 4 days ago
$180
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Apr 2 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Mon, Apr 7, priced at $180 found 4 days ago
Contour Airlines
Thu, Apr 10 - Sun, Apr 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, just found
$189
Roundtrip
just found
Select Contour Airlines flight, departing Thu, Apr 10 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Apr 13, priced at $189 just found
Delta
Tue, May 6 - Tue, May 6
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$191 Roundtrip, found 3 days ago
$191
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, May 6 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, May 6, priced at $191 found 3 days ago
Delta
Wed, May 14 - Fri, May 16
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 14 from Love Field to Midway Intl., returning Fri, May 16, priced at $197 found 1 day ago
Delta
Mon, Apr 14 - Wed, Apr 16
DAL
Love Field
ORD
O'Hare Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Apr 14 from Love Field to O'Hare Intl., returning Wed, Apr 16, priced at $197 found 1 day ago
JetBlue Airways
Sat, Jun 7 - Tue, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$355 Roundtrip, found 14 hours ago
$355
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Sat, Jun 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 10, priced at $355 found 14 hours 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 June, 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 $68, 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 $68 right now, why wait?

Crestwood Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$68

Last Minute Hotel Deals in Crestwood

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $128 per night from Mar 23 to Mar 24
$128
includes taxes & fees
Mar 23 - Mar 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! (3,934 reviews)
"Very nice and clean."

Reviewed on Mar 20, 2025

River Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is $193 per night from Mar 23 to Mar 24
$193
includes taxes & fees
Mar 23 - Mar 24
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 ...
9.6/10 Exceptional! (1,907 reviews)
"Staff was welcoming and very helpful"

Reviewed on Mar 20, 2025

L7 Chicago by LOTTE
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $164 per night from Apr 20 to Apr 21
$164
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,001 reviews)
"Friendly staff and spacious room. Easy check-in"

Reviewed on Mar 17, 2025

The Westin Michigan Avenue Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $157 per night from Mar 23 to Mar 24
$157
includes taxes & fees
Mar 23 - Mar 24
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! (8,594 reviews)
"Hotel is older- has some character. Rooms are basic but clean. No frills. Great location."

Reviewed on Mar 20, 2025

Congress Plaza Hotel
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 $120 per night from Mar 26 to Mar 27
$120
includes taxes & fees
Mar 26 - Mar 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 ...
8.6/10 Excellent! (1,004 reviews)
"We really enjoyed staying here. The parking was easy to get to. The staff was very nice and helpful. The lobby is very nice and cozy. It just seems to be an older hotel, so with age some of the fixtures/decor were out dated. That wasn't a problem for me, but it could be for some! It's in a nice area ..."

Reviewed on Mar 17, 2025

Crowne Plaza Chicago West Loop by IHG
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3 out of 5
10 E Grand Ave, Chicago, IL
The price is $125 per night from Apr 13 to Apr 14
$125
includes taxes & fees
Apr 13 - Apr 14
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (3,090 reviews)
"Nice hotel with pleasant, helpful, professional staff. I always enjoy staying there!"

Reviewed on Mar 20, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $224 per night from Mar 23 to Mar 24
$224
includes taxes & fees
Mar 23 - Mar 24
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! (1,967 reviews)
"Great"

Reviewed on Mar 20, 2025

Swissotel - Chicago
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
The price is $214 per night from Apr 6 to Apr 7
$214
includes taxes & fees
Apr 6 - Apr 7
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,715 reviews)
"Great hotel"

Reviewed on Mar 20, 2025

Hilton Chicago
See all 3,433 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.