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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $356, price is now $211 per person
$211
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,050, price is now $518 per person
$518
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $825, price is now $454 per person
$454
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $522, price is now $303 per person
$303
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $646, price is now $383 per person
$383
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

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
$116 nightly
The price is $136 total per night
$136 total
Nov 24 - Nov 25
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
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Free Cancellation
$120 nightly
The price is $141 total per night
$141 total
Nov 24 - Nov 25
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 15 conference rooms, free WiFi in public areas, and express check-in. Enjoy the sauna and conveniences like a 24-hour front desk and laundry facilities.
Pool
Free WiFi
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $119 total per night
$119 total
Nov 24 - Nov 25
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. WiFi in public areas is free.
Free WiFi
Air conditioning
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
$110 nightly
The price is $129 total per night
$129 total
Nov 16 - Nov 17
Total with taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $100 total per night
$100 total
Nov 10 - Nov 11
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $134 total per night
$134 total
Oct 30 - Oct 31
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
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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

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

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 $211, 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

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