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Crestwood Vacation Packages

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Crestwood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

4 out of 5
Price was $475, price is now $347 per person
$347
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $921, price is now $545 per person
$545
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $809, price is now $493 per person
$493
per person
Jun 1 - Jun 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,171, price is now $783 per person
$783
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was $962, price is now $671 per person
$671
per person
Jun 4 - Jun 8
found 2 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $949, price is now $663 per person
$663
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Save 100% on your flight
Price was $937, price is now $682 per person
$682
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $598, price is now $440 per person
$440
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $921, price is now $545 per person
$545
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,473, price is now $752 per person
$752
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $1,058, price is now $647 per person
$647
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,090, price is now $670 per person
$670
per person
Jun 3 - Jun 7
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.
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 $1,422, price is now $855 per person
$855
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,983, price is now $1,020 per person
$1,020
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,567, price is now $1,009 per person
$1,009
per person
Jun 4 - Jun 9
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
Tue, Apr 14 - Tue, Apr 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$106 Roundtrip, just found
$106
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Apr 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 21, priced at $106 just found
Frontier Airlines
Wed, Apr 15 - Mon, Apr 20
LAX
Los Angeles Intl.
MDW
Midway Intl.
$205 Roundtrip, just found
$205
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Apr 15 from Los Angeles Intl. to Midway Intl., returning Mon, Apr 20, priced at $205 just found
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$532 Roundtrip, just found
$532
Roundtrip
just found
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $532 just found
Asiana Airlines
Wed, Jun 3 - Mon, Sep 7
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,155 Roundtrip, found 2 hours ago
$1,155
Roundtrip
found 2 hours ago
Select Asiana Airlines flight, departing Wed, Jun 3 from Pudong Intl. to O'Hare Intl., returning Mon, Sep 7, priced at $1,155 found 2 hours ago