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Crestwood

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Crestwood Flights as Low as $68

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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.

Just the right flight

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.

Frequently Asked Questions About flights to Crestwood

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 $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?

Can I fly to Crestwood right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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

Last Minute Hotel Deals in Crestwood

Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $82 per night from Apr 29 to Apr 30
$82
per night
Apr 29 - Apr 30
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
7.8/10 Good! (1,013 reviews)
Bedbugs!!!! Terrible.
"Bedbugs were killing me and made me wake up middle of the night everyday. I need moneyback."

Reviewed on Apr 18, 2024

Hotel Felix River North/Magnificent Mile
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $143 per night from Apr 28 to Apr 29
$143
per night
Apr 28 - Apr 29
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 rooms ...
7.6/10 Good! (6,584 reviews)
"Good location"

Reviewed on Apr 21, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $149 per night from Apr 28 to Apr 29
$149
per night
Apr 28 - Apr 29
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! (2,800 reviews)
"The room wasn't done during my stay"

Reviewed on Apr 22, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $162 per night from Apr 30 to May 1
$162
per night
Apr 30 - May 1
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,858 reviews)
"The views from the room was amazing, quick access to fine dining and the staff was very friendly and welcoming."

Reviewed on Apr 21, 2024

Eurostars Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
The price is $129 per night from Apr 28 to Apr 29
$129
per night
Apr 28 - Apr 29
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the restaurant and the helpful staff ...
8.4/10 Very Good! (3,001 reviews)
Short weekend trip!
"It was a nice stay. First time in this hotel. Would come back. Only issue was the toilet stopped up twice after barely using it where we had to request maintenance. Additionally, the air conditioner never got cold. We had it turned down to 65 degrees and it never got that low. Was about 10-15 degrees ..."

Reviewed on Apr 22, 2024

Club Quarters Hotel, Central Loop, Chicago
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3 out of 5
243 E. Ontario, Chicago, IL
The price is $98 per night from Apr 28 to Apr 29
$98
per night
Apr 28 - Apr 29
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (2,179 reviews)
"Great hospitality"

Reviewed on Apr 22, 2024

Aloft Chicago Mag Mile
InterContinental Chicago Magnificent Mile, an IHG Hotel
InterContinental Chicago Magnificent Mile, an IHG Hotel
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is $204 per night from Apr 28 to Apr 29
$204
per night
Apr 28 - Apr 29
Stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
8.6/10 Excellent! (1,553 reviews)
"Excellent location, friendly staff, and outstanding pool."

Reviewed on Apr 22, 2024

InterContinental Chicago Magnificent Mile, an IHG Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $167 per night from Apr 27 to Apr 28
$167
per night
Apr 27 - Apr 28
Stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,006 reviews)
"The hotel was very nice. However, I was not expecting the $25 resort fee per day. I found it difficult to use since I was staying at the hotel for a conference. Most meals were provided. We only went to the hotel restaurant one evening for dinner."

Reviewed on Apr 21, 2024

The Westin Michigan Avenue 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.