Downtown Vacation Packages
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Top Holiday Package Deals in Downtown
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 14 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $2,061, price is now CA $1,276 per person
CA $1,276
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug. 21, 2025
SpringHill Suites by Marriott Chicago Chinatown
Chinatown
Price was CA $2,193, price is now CA $1,419 per person
CA $1,419
per person
Nov 17 - Nov 23
found 16 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (982 reviews)
Great place if you don’t have to park a car. If you do have to park, you will want a small vehicle for their parking. They contract w a public parking spot that fills up super easy and only one way in and out w no turnaround, you have to back up and do a 25 point turn to get out if no spaces available. If you are good parking in an open lot and walking, this place was wonderful and I recommend.
Reviewed on Sep. 1, 2025
Where to stay in Downtown
Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like Michigan Maritime Museum and North Beach.
Downtown Hotel Deals
Old Harbor Inn
515 Williams Street, South Haven, MI
The price is CA $222 per night from Sep 8 to Sep 9
CA $222
CA $247 total
Sep 8 - Sep 9
includes taxes & fees
Historic Hotel Nichols
201 Center St, South Haven, MI
The price is CA $258 per night from Sep 22 to Sep 23
CA $258
CA $286 total
Sep 22 - Sep 23
includes taxes & fees
The Black Pearl: industrial condo sleeps 6, full size kitchen & scenic views!
South Haven
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.