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Save up to $413 | Book Flight + Hotel at the same time^
Save up to $413 | Book Flight + Hotel at the same time^
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Save up to $413 | Book Flight + Hotel at the same time^

Crestwood Vacations

Crestwood Vacations

You've bought your plane ticket and packed your suitcase, but how much do you really know about your next exciting vacation destination? Sit back and let us give you the lowdown on Crestwood.

Crestwood is a neighborhood in the fantastic city of Chicago. To get there, travel 17 miles (27 kilometers) to the south of the downtown area.

Chicago is home to some 2,700,000 locals.

Crestwood Vacation Packages

Get a fantastic price on your trip to Crestwood by combining your accommodation and flight bookings. You can also choose from upwards of 400 partner airlines and 665,000 places to stay.

Our Customer 1st Guarantee gives you the security of 24/7 personal assistance on everything from airfares and accommodations to car rentals and activities. If you somehow stumble upon a lower price on another website, we will refund the difference^.

You never know if something will come up. However, if you book a package, we guarantee no scary hidden fees from us. And so long as you get in quick, most accommodations won't charge a fee either^.

Hotels in Crestwood

If you have your heart set on staying around the center of Crestwood, Travelocity has what you're looking for. With that being said, we only have 4 listed properties, so it's a good idea to book ASAP. Lock in your room of choice and then start looking forward to the fun stuff!

Check out the deals on offer at the DoubleTree by Hilton Chicago - Alsip (5000 W 127th St) and the Holiday Inn Express Crestwood (13330 South Cicero Avenue). They're our top suggestions.

Where do you fly into for Crestwood?

Flying into Midway International Airport (MDW)? Crestwood is just 10 miles (16 kilometers) away. Grab some nibbles, flag down a cab and you'll arrive in no time!

Can I rent a car in Crestwood?

Tickets to Crestwood? Check. Road trip playlists? Check. Now the only thing left is to pick a set of wheels via Travelocity. You'll be on the road in no time!

Picking up the car keys from Midway International Airport means you'll be out of the air and into the driver's seat in minutes. You won't have to go far to find Budget and Avis.

If you have plans to stay in the city, go to Enterprise at 12055 S. Cicero. It is positioned 2 miles (3 kilometers) from the heart of town.

Places to visit in Crestwood

Nothing compares to being in nature, and the wider region offers some superb outdoor adventures to try. How about a little mountain biking?

The fun doesn't need to end there. Think about finding time to go rock climbing too.

Places to Visit Near Crestwood

Oak Forest and Goeselville are well worth visiting while you are here. Oak Forest is around 3 miles (5 kilometers) away, and Goeselville is 3 miles (5 kilometers) away.

^Terms and conditions apply.

Top Crestwood Hotels Deals

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 out of 5.0 701 North Michigan Avenue, Chicago, IL
(232 Reviews)
This hotel features a restaurant, a 24-hour fitness center, and a bar/lounge. Families will appreciate the onsite laundry facilities and supervised childcare. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5.0 520 South Michigan Avenue, Chicago, IL
(101 Reviews)
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and fitness center are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and express check-in are also offered.
Holiday Inn Express Crestwood

Holiday Inn Express Crestwood

2.5 out of 5.0 13330 South Cicero Avenue, Crestwood, IL
(11 Reviews)
This hotel features an indoor pool and a fitness center. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Things to do in Crestwood

See all 223 things to do in Crestwood

Top Flight Deals to Crestwood

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

^Savings based on all package bookings made with Flight + Hotel on from January 1, 2018 to December 31, 2018, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.