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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $690, price is now $415 per person
$415
per person
Nov 6 - Nov 8
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.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $971, price is now $587 per person
$587
per person
Nov 13 - Nov 15
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $1,816, price is now $1,165 per person
$1,165
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
It is the greatest will be there again

Reviewed on Sep 29, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $848, price is now $556 per person
$556
per person
Dec 2 - Dec 6
found 14 hours 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.
👍

Reviewed on Sep 28, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,035, price is now $692 per person
$692
per person
Dec 22 - Dec 27
found 2 days 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.
Amables y todo cerca

Reviewed on Sep 30, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $908, price is now $611 per person
$611
per person
Nov 6 - Nov 9
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.
Amazing view, very clean room

Reviewed on Sep 30, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $776, price is now $532 per person
$532
per person
Nov 6 - Nov 8
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.

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $943, price is now $650 per person
$650
per person
Nov 20 - Nov 23
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.

Crestwood Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $698, price is now $418 per person
$418
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,261, price is now $732 per person
$732
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,816, price is now $1,165 per person
$1,165
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $848, price is now $556 per person
$556
per person
Dec 2 - Dec 6
found 14 hours 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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,327, price is now $886 per person
$886
per person
Nov 4 - Nov 9
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,822, price is now $1,140 per person
$1,140
per person
Nov 4 - Nov 9
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,759, price is now $1,123 per person
$1,123
per person
Dec 22 - Dec 27
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,424, price is now $929 per person
$929
per person
Oct 30 - Nov 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Thu, Oct 15 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$122 Roundtrip, found 3 hours ago
$122
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Oct 15 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $122 found 3 hours ago
United
Fri, Nov 13 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select United flight, departing Fri, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 found 4 hours ago
Southwest Airlines
Mon, Nov 9 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$200 Roundtrip, found 4 hours ago
$200
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Mon, Nov 9 from Los Angeles Intl. to Midway Intl., returning Fri, Nov 13, priced at $200 found 4 hours ago
Philippine Airlines
Fri, Nov 13 - Wed, Nov 25
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,072 Roundtrip, found 4 hours ago
$1,072
Roundtrip
found 4 hours ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Nov 25, priced at $1,072 found 4 hours ago