Deals on vacations and trips to Crestwood

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Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

2.5 out of 5
Ashburn
Save 100% on your flight
Price was $672, price is now $462 per person
$462
per person
Sep 3 - Sep 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A gym is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
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 $760, price is now $487 per person
$487
per person
Sep 19 - Sep 22
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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,120, price is now $746 per person
$746
per person
Sep 3 - Sep 6
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. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,105, price is now $746 per person
$746
per person
Sep 12 - Sep 15
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, laundry facilities, and concierge services are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,365, price is now $925 per person
$925
per person
Aug 6 - Aug 9
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

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
$136 nightly
The price is $162 total per night
$162 total
Jun 30 - Jul 1
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
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$181 nightly
The price is $215 total per night
$215 total
Jul 5 - Jul 6
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. There's in-room fitness on site, and concierge services and wedding services are also offered.
Pet friendly
Free WiFi
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$141 nightly
The price is $167 total per night
$167 total
Jul 7 - Jul 8
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$194 nightly
The price is $231 total per night
$231 total
Jul 5 - Jul 6
Total with taxes and fees
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.
Breakfast included
Free WiFi
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
$115 nightly
The price is $137 total per night
$137 total
Jul 1 - Jul 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.
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $185 total per night
$185 total
Jul 5 - Jul 6
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.
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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.

Popular places to visit

An aerial view of a baseball stadium surrounded by urban buildings and streets.

Wrigley Field

4.5/5(2,149 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
A coastal cityscape with high-rise buildings, a marina, and a park area.

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
A Ferris wheel and a carousel at a fairground.

Navy Pier

4.5/5(4,925 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Frequently asked questions

How much are vacation packages to Crestwood?
With vacation packages on offer from as little as $462, 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.