Deals on vacations and trips to Crestwood

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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $504, price is now $308 per person
$308
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out 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 $1,523, price is now $860 per person
$860
per person
Nov 5 - Nov 9
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $975, price is now $605 per person
$605
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $724, price is now $472 per person
$472
per person
Dec 12 - Dec 16
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Dry cleaning, luggage storage, and wedding services are also on offer.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $814, price is now $532 per person
$532
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

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
$107 nightly
The price is $127 total per night
$127 total
Nov 2 - Nov 3
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.
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$167 nightly
The price is $199 total per night
$199 total
Nov 1 - Nov 2
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.
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
Nov 1 - Nov 2
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
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $169 total per night
$169 total
Oct 4 - Oct 5
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$190 nightly
The price is $226 total per night
$226 total
Oct 30 - Oct 31
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $171 total per night
$171 total
Nov 1 - Nov 2
Total with taxes and fees
A full-service spa and a gym are featured at this boutique hotel. 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 express check-out are also provided.
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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.
See properties

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.