Search Deals on
Crestwood Vacation Packages

Build your package with 2 more options

Crestwood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $452, price is now $250 per person
$250
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star golf hotel in Downers Grove. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Morton Arboretum and Yorktown Shopping Center are located nearby.
Art Villa

Art Villa

5 out of 5
Save 100% on your flight
Price was $1,004, price is now $473 per person
$473
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 5-star luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,136, price is now $585 per person
$585
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $500, price is now $266 per person
$266
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,078, price is now $585 per person
$585
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $990, price is now $546 per person
$546
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $475, price is now $268 per person
$268
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,306, price is now $788 per person
$788
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Crestwood Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
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 $500, price is now $266 per person
$266
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,004, price is now $473 per person
$473
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $718, price is now $386 per person
$386
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $536, price is now $307 per person
$307
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Crestwood Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
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 $674, price is now $366 per person
$366
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,728, price is now $744 per person
$744
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,136, price is now $585 per person
$585
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $585 per person
$585
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Fri, Nov 14 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $74 found 1 day ago
Spirit Airlines
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 4 hours ago
$110
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $110 found 4 hours ago
Frontier Airlines
Thu, Oct 30 - Mon, Nov 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Los Angeles Intl. to Midway Intl., returning Mon, Nov 3, priced at $170 found 5 days ago
All Nippon Airways
Wed, Nov 5 - Mon, Dec 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$999 Roundtrip, found 2 days ago
$999
Roundtrip
found 2 days ago
Select All Nippon Airways flight, departing Wed, Nov 5 from Pudong Intl. to O'Hare Intl., returning Mon, Dec 1, priced at $999 found 2 days ago