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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,619, price is now CA $1,072 per person
CA $1,072
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,646, price is now CA $1,608 per person
CA $1,608
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
Picked the hotel because it was supposed to be near Riviera theater. It really wasn't. Otherwise, it's a beautiful property. Staff are friendly and helpful. There's casual and fine dining at the location. Easy to get a cab if you don't have an app. Across from riverfront.

Reviewed on May 9, 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 $3,324, price is now CA $2,155 per person
CA $2,155
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $2,831, price is now CA $1,940 per person
CA $1,940
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Great property and location!

Reviewed on May 8, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $2,242, price is now CA $1,541 per person
CA $1,541
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,655 reviews)
If you’re up for walking, this hotel is a great place to stay close enough to most things.

Reviewed on May 8, 2026

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Westchester Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $430 per night from Jun 7 to Jun 8
CA $430
CA $553 total
Jun 7 - Jun 8
includes taxes & fees
8.2/10 Very Good! (2,697 reviews)
great location

Reviewed on May 9, 2026

Hotel Felix River North/Magnificent Mile
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 $183 per night from May 11 to May 12
CA $183
CA $217 total
May 11 - May 12
includes taxes & fees
8/10 Very Good! (10,191 reviews)
Rude, staffs, not responding to house service/room service. Poor service, flush kept on leaking. Very very terrible condition of the room.

Reviewed on May 9, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from May 26 to May 27
CA $208
CA $247 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,191 reviews)
I can only review the staff at The River Hotel is AMAZING to say the least. From the moment I walked through the door I felt at home. I received a warm welcome and a fabulous room with all of the amenities. My room (suite) was spacious, clean and so comfortable. The hotel is centrally located so ...

Reviewed on May 9, 2026

River Hotel
See all 5,167 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

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

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
Navy Pier

Navy Pier

4.5/5(460 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Westchester

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.