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Highwood
Chicago
Illinois
United States of America
North America
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Highwood Flight + Hotel Packages

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

Hollywood Casino Aurora

2 out of 5

Price was $1,531, price is now $392 per person

$392

per person

Jul 27 - Jul 30

found 1 hour ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this spa hotel in Aurora. Enjoy a full-service spa, 9 restaurants, and valet parking (surcharge). Popular attractions Chicago Premium Outlets and Red Oak Nature Center are located nearby.

Level Chicago Fulton Market

4 out of 5

Save 100% on your flight

Price was $1,557, price is now $977 per person

$977

per person

Aug 4 - Aug 8

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 parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Level Chicago – Old Town

4 out of 5

Save 100% on your flight

Price was $1,374, price is now $906 per person

$906

per person

Jul 10 - Jul 13

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.

Level Chicago - River North

4 out of 5

Save 100% on your flight

Price was $1,315, price is now $879 per person

$879

per person

Jul 30 - Aug 2

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.

Urban Chicago Oasis

2 out of 5

Save 100% on your flight

Price was $1,322, price is now $906 per person

$906

per person

Jul 30 - Aug 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Waldorf Astoria Chicago

5 out of 5

Save 100% on your flight

Price was $1,936, price is now $1,359 per person

$1,359

per person

Jul 10 - Jul 13

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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5

Price was $676, price is now $479 per person

$479

per person

Jul 8 - Jul 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this business-friendly 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 Chicago Riverwalk and Millennium Park are located nearby.

Trump International Hotel & Tower Chicago

5 out of 5

Save 100% on your flight

Price was $1,419, price is now $1,012 per person

$1,012

per person

Jul 17 - Jul 20

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.