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Westchester Vacation Packages

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Westchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $919, price is now $588 per person
$588
per person
Jul 1 - Jul 5
found 2 days 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was $1,744, price is now $874 per person
$874
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Wade

The Wade

4.5 out of 5
Price was $1,754, price is now $969 per person
$969
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,976, price is now $1,139 per person
$1,139
per person
Jun 17 - Jun 23
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, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,997, price is now $1,187 per person
$1,187
per person
Jun 17 - Jun 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, a full-service spa, and 2 restaurants. 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

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,052, price is now $636 per person
$636
per person
Jul 1 - Jul 5
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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,493, price is now $946 per person
$946
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,768, price is now $1,121 per person
$1,121
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Westchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $807, price is now $543 per person
$543
per person
Jul 23 - Jul 26
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,052, price is now $636 per person
$636
per person
Jul 1 - Jul 5
found 2 days 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 $919, price is now $588 per person
$588
per person
Jul 1 - Jul 5
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,319, price is now $858 per person
$858
per person
Jul 23 - Jul 26
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Westchester Vacation Packages 5-7 Night Stays

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,744, price is now $874 per person
$874
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $2,031, price is now $1,045 per person
$1,045
per person
Jun 17 - Jun 23
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 $1,922, price is now $1,056 per person
$1,056
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was $1,754, price is now $969 per person
$969
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Delta
Wed, Aug 12 - Tue, Aug 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 20 hours ago
$134
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Aug 12 from Los Angeles Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $134 found 20 hours ago
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$219 Roundtrip, found 21 hours ago
$219
Roundtrip
found 21 hours ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Midway Intl., returning Wed, Jul 29, priced at $219 found 21 hours ago
American Airlines
Sun, May 24 - Sun, May 31
LAX
Los Angeles Intl.
RFD
Greater Rockford
$404 Roundtrip, found 19 hours ago
$404
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sun, May 24 from Los Angeles Intl. to Greater Rockford, returning Sun, May 31, priced at $404 found 19 hours ago
Turkish Airlines
Wed, Jul 8 - Wed, Jul 15
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$823 Roundtrip, found 2 hours ago
$823
Roundtrip
found 2 hours ago
Select Turkish Airlines flight, departing Wed, Jul 8 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Wed, Jul 15, priced at $823 found 2 hours ago