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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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $972, price is now $647 per person
$647
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 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 $1,072, price is now $669 per person
$669
per person
Oct 1 - Oct 4
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 $1,079, price is now $694 per person
$694
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,455, price is now $967 per person
$967
per person
Oct 21 - Oct 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, 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.
Great location!

Reviewed on Jul 31, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $938, price is now $651 per person
$651
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities

Reviewed on Jul 30, 2026

Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
Price was $1,320, price is now $920 per person
$920
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and balconies or patios. Popular attractions Wrigley Field and Michigan Avenue are located nearby.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,035, price is now $731 per person
$731
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,061, price is now $753 per person
$753
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
I really loved this hotel

Reviewed on Jul 31, 2026

Crestwood Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $855, price is now $491 per person
$491
per person
Oct 2 - Oct 6
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
Save 100% on your flight
Price was $1,072, price is now $669 per person
$669
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 $835, price is now $531 per person
$531
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,079, price is now $694 per person
$694
per person
Oct 6 - Oct 9
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 $1,647, price is now $905 per person
$905
per person
Oct 15 - Oct 21
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,024, price is now $1,111 per person
$1,111
per person
Oct 15 - Oct 21
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,963, price is now $1,112 per person
$1,112
per person
Oct 15 - Oct 21
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,572, price is now $2,087 per person
$2,087
per person
Sep 12 - Sep 19
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
Sat, Sep 5 - Tue, Sep 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $171 found 2 hours ago
Frontier Airlines
Thu, Aug 27 - Sat, Sep 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$233 Roundtrip, found 2 hours ago
$233
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Aug 27 from Los Angeles Intl. to Midway Intl., returning Sat, Sep 5, priced at $233 found 2 hours ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 22 hours ago
$250
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $250 found 22 hours ago
Hainan Airlines
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,128 Roundtrip, found 22 hours ago
$1,128
Roundtrip
found 22 hours ago
Select Hainan Airlines flight, departing Tue, Sep 1 from Capital Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $1,128 found 22 hours ago