Deals on vacations and trips to Westchester
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Westchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $868, price is now $523 per person
$523
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,105, price is now $643 per person
$643
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,347, price is now $824 per person
$824
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,071, price is now $695 per person
$695
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $805, price is now $532 per person
$532
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Top Westchester hotels deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $173 total per night
$173 total
Jun 29 - Jun 30
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Free Cancellation
$154 nightly
The price is $183 total per night
$183 total
Jun 28 - Jun 29
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Business travelers can take advantage of the free WiFi in public areas. Self parking, express check-out, and luggage storage are also offered.
Pet friendly
Free WiFi
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$203 nightly
The price is $242 total per night
$242 total
Jun 30 - Jul 1
Total with taxes and fees
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Breakfast included
Free WiFi
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $154 total per night
$154 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.
Free airport shuttle
Pet friendly
Freehand Chicago
19 East Ohio Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$137 nightly
The price is $162 total per night
$162 total
Jul 6 - Jul 7
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$162 nightly
The price is $192 total per night
$192 total
Jun 29 - Jun 30
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.
Pet friendly
Free WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Frequently asked questions
Photos of local treasures
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