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 – Old Town
Downtown Chicago
Price was CA $1,727, price is now CA $1,204 per person
CA $1,204
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $3,802, price is now CA $2,621 per person
CA $2,621
per person
Aug 1 - Aug 5
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views
Reviewed on Jun 22, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,442, price is now CA $1,689 per person
CA $1,689
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on Jun 23, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,376, price is now CA $1,714 per person
CA $1,714
per person
Aug 3 - Aug 7
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $2,178, price is now CA $1,591 per person
CA $1,591
per person
Aug 26 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026
Westchester Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Jun 29 to Jun 30
CA $194
CA $230 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (10,175 reviews)
"excellent location. Majority of the room is renovated but some part are still look worn"
Reviewed on Jun 24, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Jul 5 to Jul 6
CA $209
CA $248 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (4,454 reviews)
"Good location, bar and brunch were great. View from the pool and fitness centers was u real. Room was clean but sink faucet was loose and leaking and the bathroom door locks didn’t work well or would stick. Other than that it was nice."
Reviewed on Jun 24, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jun 30 to Jul 1
CA $179
CA $212 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,623 reviews)
"Great location! Very close to Magnificent Mile, restaurant's, and the Museum of Ice Cream. The showers are really tight. Other than that the junior suite was perfect for the price and location. I would definitely book again."
Reviewed on Jun 24, 2026
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.
Discover the most popular places to visit in Westchester
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Westchester
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $69
per adult
94% of travellers recommend
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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.
