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Crestwood Vacation Packages

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A serene lake with reflections of trees and a cloudy sky.

Crestwood
Chicago
Illinois
United States of America
North America
Hotwire.com

Crestwood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile

4 out of 5

Save 100% on your flight

Price was $713, price is now $449 per person

$449

per person

Nov 4 - Nov 8

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.

Excellent hotel, great location.

Reviewed on Sep 30, 2026

Hotel Riu Plaza Chicago

4 out of 5

Save 100% on your flight

Price was $1,436, price is now $831 per person

$831

per person

Nov 4 - 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 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

Trump International Hotel & Tower Chicago

5 out of 5

Save 100% on your flight

Price was $1,819, price is now $1,063 per person

$1,063

per person

Nov 4 - 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, 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.

Kimpton Gray Hotel by IHG

4.5 out of 5

Save 100% on your flight

Price was $1,104, price is now $704 per person

$704

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

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

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 9 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

The Talbott, Autograph Collection

4.5 out of 5

Save 100% on your flight

Price was $1,109, price is now $730 per person

$730

per person

Nov 4 - 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.

Sports Illustrated Resorts Chicago

3.5 out of 5

Save 100% on your flight

Price was $785, price is now $518 per person

$518

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.