Search Deals on
Crestwood Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

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.

theWit Chicago, a Hilton Hotel

4.5 out of 5

Save 100% on your flight

Price was $311, price is now $144 per person

$144

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Pendry Chicago

4.5 out of 5

Save 100% on your flight

Price was $470, price is now $232 per person

$232

per person

Jan 23 - Jan 26

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.

Level Chicago – Old Town

4 out of 5

Price was $1,087, price is now $558 per person

$558

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Stay at this 4-star 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

4 out of 5

Price was $442, price is now $230 per person

$230

per person

Jan 23 - Jan 26

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.

Trump International Hotel & Tower Chicago

5 out of 5

Price was $766, price is now $422 per person

$422

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Hotel Riu Plaza Chicago

4 out of 5

Save 100% on your flight

Price was $348, price is now $194 per person

$194

per person

Jan 23 - Jan 26

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.

Park Hyatt Chicago

5 out of 5

Save 100% on your flight

Price was $824, price is now $468 per person

$468

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5

Price was $710, price is now $420 per person

$420

per person

Dec 23 - Dec 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, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.