Deals on vacations and trips to Crestwood

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Crestwood flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was $554, price is now $308 per person
$308
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a coffee shop, and free WiFi in public areas. Express check-out, luggage storage, and free newspapers are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $682, price is now $395 per person
$395
per person
Sep 23 - Sep 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,008, price is now $595 per person
$595
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $583, price is now $364 per person
$364
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a computer station, and dry cleaning are also offered.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,876, price is now $1,179 per person
$1,179
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.

Top Crestwood hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $130 total per night
$130 total
Sep 8 - Sep 9
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $170 total per night
$170 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.
Pet friendly
Free WiFi
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Get rates
A gym, self parking, and a virtual front desk are featured at this aparthotel. WiFi in public areas is free. A convenience store and luggage storage are also provided.
Kitchen
Washer
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $251 total per night
$251 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and a coffee shop are also provided.
Free WiFi
Restaurant
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $195 total per night
$195 total
Aug 31 - Sep 1
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$222 nightly
The price is $264 total per night
$264 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a lobby fireplace, and luggage storage are also offered.
Pet friendly
Free WiFi
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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.

Stay near popular Crestwood attractions

Hollywood Park

Have a fun-filled day with the family at Hollywood Park as part of your trip to Crestwood. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
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Frequently asked questions

How much are vacation packages to Crestwood?
With vacation packages on offer from as little as $308, you won't need to empty your piggy bank for your visit to Crestwood. Travelocity can help. Combine hotels, flights and experiences into a convenient package and land some excellent discounts. The more you book, the greater the savings.
How long should my Crestwood vacation be?
Many travelers pack their suitcase and see the sights of Crestwood for an average of 2 nights. That's a good starting point, but don't feel restricted by it. Whether you just stay for a few days to see the famous attractions or linger a while to discover the lesser-known sights, an amazing getaway awaits.
Where can I get the best vacation package deals for Crestwood?
It's simple — head to Travelocity. With 400 air carriers and 1,000,000 worldwide properties, it's a breeze to find a Crestwood package deal that satisfies your wanderlust.
Why should I book my Crestwood vacation package with Travelocity?
Whether you're planning a month-long vacation or a last-minute weekend trip, we have many amazing destinations to choose from at a fantastic price. What's more, we provide customer support 24/7, excellent service and a Price Match Guarantee. Save yourself the effort and time and book your dream vacation now.
Can I save on my Crestwood car rental if I combine it with my hotel or flight?
Bundling your car, hotel and flight into a Crestwood vacation package is an easy way to land the best prices. Plus, having your own rental car gives you absolute freedom to make your way to all those big-name sights you're hoping to check out. Located 50 mi from Crestwood, Six Flags Great America is one attraction that should be on your to-do list. Fill up the tank and make a day trip of it.
Which airport is best for Crestwood?
For many travelers, heading to Crestwood means coming in to land at O'Hare Intl. Airport (ORD). This busy airport is located 25 mi north of the city center. You could also opt to jet into Midway Intl. Airport (MDW) (9 mi away from central Crestwood) or Lewis University Airport (LOT) (18 mi away from central Crestwood).
Where should I stay when visiting Crestwood?
Many visitors choose to spend their nights at the Holiday Inn Express Crestwood, an IHG Hotel. It's the perfect base for your Crestwood escape.

Photos of local treasures

Browse Crestwood vacation photos for more inspiration

A serene lake with reflections of trees and a cloudy sky.