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Westchester Flight + Hotel Packages

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

The Stella Hotel & Ballroom

3.5 out of 5

Price was $472, price is now $350 per person

$350

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

New York (LGA) to Chicago (CHI)

Stay at this 3.5-star business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dinosaur Discovery Museum and Alpaca Art are located nearby.

Hotel Riu Plaza Chicago

4 out of 5

Save 100% on your flight

Price was $659, price is now $412 per person

$412

per person

Nov 7 - Nov 10

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.

Level Chicago Fulton Market

4 out of 5

Save 100% on your flight

Price was $1,024, price is now $664 per person

$664

per person

Nov 28 - Dec 3

found 17 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Trump International Hotel & Tower Chicago

5 out of 5

Save 100% on your flight

Price was $1,149, price is now $772 per person

$772

per person

Nov 7 - Nov 10

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.

Park Hyatt Chicago

5 out of 5

Save 100% on your flight

Price was $1,066, price is now $771 per person

$771

per person

Oct 31 - Nov 2

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.

Fairmont Chicago at Millennium Park

4.5 out of 5

Save 100% on your flight

Price was $682, price is now $505 per person

$505

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this spa 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 Millennium Park and Chicago Riverwalk are located nearby.

Urban Chicago Oasis

2 out of 5

Save 100% on your flight

Price was $1,949, price is now $1,443 per person

$1,443

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5

Save 100% on your flight

Price was $768, price is now $569 per person

$569

per person

Oct 24 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.