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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.
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $819, price is now $467 per person
$467
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,024, price is now $499 per person
$499
per person
Dec 30 - Jan 6
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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,164, price is now $569 per person
$569
per person
Dec 30 - Jan 6
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.
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 $1,119, price is now $609 per person
$609
per person
Nov 25 - Dec 2
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, 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $910, price is now $500 per person
$500
per person
Dec 30 - Jan 6
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $994, price is now $557 per person
$557
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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 Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,312, price is now $748 per person
$748
per person
Nov 25 - Dec 2
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

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,123, price is now $659 per person
$659
per person
Dec 5 - Dec 8
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.

Westchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $541, price is now $348 per person
$348
per person
Dec 23 - Dec 26
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,123, price is now $659 per person
$659
per person
Dec 5 - Dec 8
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
Save 100% on your flight
Price was $577, price is now $350 per person
$350
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $911, price is now $604 per person
$604
per person
Dec 22 - Dec 26
found 7 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $910, price is now $500 per person
$500
per person
Dec 30 - Jan 6
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 $1,841, price is now $844 per person
$844
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,164, price is now $569 per person
$569
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,119, price is now $609 per person
$609
per person
Nov 25 - Dec 2
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.

Frontier Airlines
Fri, Oct 31 - Thu, Nov 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Los Angeles Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $68 found 1 day ago
Spirit Airlines
Fri, Nov 7 - Tue, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 2 hours ago
$110
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Fri, Nov 7 from Los Angeles Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $110 found 2 hours ago
Frontier Airlines
Wed, Oct 29 - Mon, Nov 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$120 Roundtrip, found 4 days ago
$120
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Oct 29 from Los Angeles Intl. to Midway Intl., returning Mon, Nov 3, priced at $120 found 4 days ago
Turkish Airlines
Tue, Nov 4 - Thu, Dec 4
PVG
Pudong Intl.
ORD
O'Hare Intl.
$948 Roundtrip, found 1 day ago
$948
Roundtrip
found 1 day ago
Select Turkish Airlines flight, departing Tue, Nov 4 from Pudong Intl. to O'Hare Intl., returning Thu, Dec 4, priced at $948 found 1 day ago