Western Suburbs Vacation Packages

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Your Western Suburbs Vacation

Embrace a world of new experiences with a Western Suburbs vacation package. This destination's unique charm and history are sure to be among the most memorable parts of your escape. A trip to Western Suburbs wouldn't be complete without spending some time in Naperville. This city is among the leading places to visit here. From the instant you book your Western Suburbs vacation to when you get back home, Expedia has your back every step of the way.

Top Western Suburbs Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,415, price is now CA $828 per person
CA $828
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly

Reviewed on Aug. 29, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $4,139, price is now CA $2,373 per person
CA $2,373
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,824, price is now CA $1,643 per person
CA $1,643
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug. 29, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,012, price is now CA $1,767 per person
CA $1,767
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,883, price is now CA $1,120 per person
CA $1,120
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

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Western Suburbs Hotel Deals

DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Sep 7 to Sep 8
CA $114
CA $127 total
Sep 7 - Sep 8
includes taxes & fees
DoubleTree by Hilton Lisle Naperville
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
The price is CA $209 per night from Sep 20 to Sep 21
CA $209
CA $245 total
Sep 20 - Sep 21
includes taxes & fees
Marriott Chicago O'Hare
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Sep 20 to Sep 21
CA $246
CA $289 total
Sep 20 - Sep 21
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 2,609 properties in Western Suburbs
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Western Suburbs

Morton Arboretum which includes wild flowers

Morton Arboretum

Leave the skyscrapers of Chicago behind by escaping inland to tranquil gardens that feature model railroads, a vast array of trees and peaceful ponds.

Morton Arboretum
Centennial Beach which includes a pool

Centennial Beach

Just outside Chicago, this beloved summer hangout features an enormous pool, volleyball courts, barbecue pits, swim lessons and much more.

Centennial Beach

Arcada Theater

You can get tickets for a performance at Arcada Theater during your stay in St. Charles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

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