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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $721, price is now $420 per person
$420
per person
Nov 11 - Nov 14
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,302, price is now $791 per person
$791
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,212, price is now $746 per person
$746
per person
Nov 11 - Nov 14
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,877, price is now $1,171 per person
$1,171
per person
Oct 15 - Oct 20
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 $730, price is now $471 per person
$471
per person
Nov 12 - Nov 15
found 1 day 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.

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
$112 nightly
The price is $133 total per night
$133 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
$188 nightly
The price is $223 total per night
$223 total
Sep 29 - Sep 30
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
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$175 nightly
The price is $208 total per night
$208 total
Sep 8 - Sep 9
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
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$178 nightly
The price is $211 total per night
$211 total
Sep 9 - Sep 10
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and valet parking. Enjoy the free continental breakfast each morning. Express check-in, express check-out, and a computer station are also on offer.
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$224 nightly
The price is $266 total per night
$266 total
Sep 8 - Sep 9
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.
Pool
Hot Tub
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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 $420, 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.