Deals on vacations and trips to Crestwood

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Crestwood flight + hotel vacation packages

Prices and availability subject to change. Additional terms may apply.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 11 - Jul 15
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the gym and perks like free WiFi.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 6
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, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a computer station are also offered.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 11 - Jul 15
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 5 - Jul 8
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.

Top Crestwood hotel 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
The price is $127 per night
$127
per night
Apr 28 - Apr 29
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.
Breakfast available
Parking available
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $139 per night
$139
per night
Apr 28 - Apr 29
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
Parking available
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $160 per night
$160
per night
Apr 28 - Apr 29
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $82 per night
$82
per night
Apr 29 - Apr 30
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Parking available
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $129 per night
$129
per night
Apr 28 - Apr 29
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.
Pet friendly
Breakfast available
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $98 per night
$98
per night
Apr 28 - Apr 29
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli are also offered.
Pet friendly
Breakfast available
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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

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(4,870 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?
Spoil yourself with a memorable travel experience in Crestwood with a vacation package starting at $327. Locking in your hotels, tours and flights through Travelocity has never been so easy. And even better, our vacation deals will leave you with more money in your pocket for loads of fun times.
How long should my Crestwood vacation be?
The majority of people opt to spend around 2 nights in Crestwood, but it’s ultimately up to you. If you’re eager to explore all the incredible things this place has waiting for you, why not hang around another night or two?
Where can I get the best vacation package deals for Crestwood?
Whatever your travel style, Travelocity can help you lock in a great Crestwood package deal. The only thing you need to do is select a combination from our 400 airlines and 1,000,000 properties across the globe.
Why should I purchase my Crestwood vacation package with Travelocity?
With first-rate service, support available 24/7 and some of the most perfect getaways around, you’ll never wander alone. And if you find a cheaper price, we’ll match it. That’s our Price Match Guarantee.
Can I save on my Crestwood car rental if I combine it with my hotel or flight?
With a Crestwood vacation package, you can bundle your car, hotel and flight bookings and save loads. When you’re ready to see the best of this impressive city, why not make a beeline for Six Flags Great America? This famous sight is 50 mi from Crestwood. With a rental car, you’ll be there belong long.
What is the best time of year to go to Crestwood?
You’ll be able to avoid the tourist hordes and save a tidy sum in December, January and February, the quietest period to visit. High season months of March, May and June are hectic and more expensive, but there’ll be more happening around Crestwood. Organize a hotel in and get plenty more bang for your buck. Room rates are usually higher in .
Which airport is best for Crestwood?
O’Hare Intl. Airport (ORD) is a major hub. It’s located approximately 25 mi north of Crestwood. Other options worth considering are Midway Intl. Airport (MDW) (9 mi away from central Crestwood) and Lewis University Airport (LOT) (18 mi away from central Crestwood).
Where should I stay when visiting Crestwood?
The Holiday Inn Express Crestwood, an IHG Hotel is popular with many visitors. Book soon before it’s too late.