Westchester Vacation Packages

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Your Westchester Vacation

A great way to experience this lively city is with a tailor-made Westchester vacation package. Stay in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our package deals are all about you. A trip to Westchester is a great opportunity to sightsee. Be sure to visit renowned attractions like Brookfield Zoo, Oakbrook Center Mall and Frank Lloyd Wright Historic District. Don't put off your visit to this city any longer. The perfect Westchester vacation is only a few clicks away with Expedia.

Top Westchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
Price was CA $1,429, price is now CA $1,057 per person
CA $1,057
per person
Jun 3 - Jun 9
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,318 reviews)
During off season not as many activities

Reviewed on Mar 16, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,311, price is now CA $1,451 per person
CA $1,451
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.

Reviewed on Mar 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,293, price is now CA $1,451 per person
CA $1,451
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Clean room. Very friendly staff

Reviewed on Mar 25, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,347, price is now CA $1,510 per person
CA $1,510
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Rooms are nice, great view, valet parking is great

Reviewed on Mar 24, 2026

Lodge Geneva National

Lodge Geneva National

4 out of 5
Price was CA $1,972, price is now CA $1,404 per person
CA $1,404
per person
Jun 3 - Jun 9
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,366 reviews)
It was ok rooms were noisy can here everything in hall and in next room

Reviewed on Mar 23, 2026

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Westchester Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Apr 1 to Apr 2
CA $159
CA $187 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (10,015 reviews)
Very nice.

Reviewed on Mar 25, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Apr 6 to Apr 7
CA $182
CA $252 total
Apr 6 - Apr 7
includes taxes & fees
9.4/10 Exceptional! (3,627 reviews)
Clean room. Very friendly staff

Reviewed on Mar 25, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Apr 13 to Apr 14
CA $175
CA $205 total
Apr 13 - Apr 14
includes taxes & fees
8.6/10 Excellent! (5,768 reviews)
I had a great time staying here. Its location made it easy to explore the downtown area on foot. Lots of cool restaurants near by. The room was spacious and staff were very friendly. The airport is far away and with the traffic, would suggest reserving extra time while traveling to the airport. All ...

Reviewed on Mar 24, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,091 properties in Westchester
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.
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Discover the most popular places to visit in Westchester

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Chicago Skyline at North Beach

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.

Naval Base Great Lakes

What to do in Westchester

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Westchester

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.