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.
Motel Edgebrook Chicago North Shore by OYO
Forest Glen
Price was $411, price is now $311 per person
$311
per person
Apr 15 - Apr 20
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Free self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. Express check-out and a safe deposit box are also provided.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $630, price is now $423 per person
$423
per person
Apr 10 - Apr 13
found 2 days 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $801, price is now $596 per person
$596
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Moxy Chicago Downtown
Downtown Chicago
Save 100% on your flight
Price was $427, price is now $319 per person
$319
per person
Mar 8 - Mar 11
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. WiFi in public areas is free. A 24-hour business center, a snack bar/deli, and a grocery/convenience store are also on offer.
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,573, price is now $1,191 per person
$1,191
per person
Apr 19 - Apr 23
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the indoor pool and perks like a free area shuttle.
Top Crestwood hotels deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $104 total per night
$104 total
Jan 31 - Feb 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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $124 total per night
$124 total
Feb 5 - Feb 6
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$133 nightly
The price is $156 total per night
$156 total
Feb 11 - Feb 12
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
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $182 total per night
$182 total
Feb 1 - Feb 2
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
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $100 total per night
$100 total
Feb 1 - Feb 2
Total with taxes and fees
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.
Pool
Pet friendly
Pendry Chicago
230 North Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$205 nightly
The price is $241 total per night
$241 total
Feb 8 - Feb 9
Total with taxes and fees
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.
Pet friendly
Free WiFi
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
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.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
McCormick Place
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.
Frequently asked questions
Photos of local treasures
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