Southwest Side Vacation Packages
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Top Southwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,309, price is now CA $837 per person
CA $837
per person
Oct 19 - Oct 22
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
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,197, price is now CA $1,334 per person
CA $1,334
per person
Nov 5 - Nov 8
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Arlo Chicago
Downtown Chicago
Price was CA $1,416, price is now CA $905 per person
CA $905
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,844 reviews)
Good spot, convenient to everything. Staff was helpful. Very urban so some issues with people begging for money etc.
Reviewed on Sep. 3, 2025
Level Chicago - River North
Downtown Chicago
Price was CA $1,489, price is now CA $964 per person
CA $964
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (672 reviews)
Loved my stay here, beautiful hotel, great amenities, friendly staff super accommodating
Reviewed on Sep. 1, 2025
Where to stay in Southwest Side
Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side
Back of the Yards
2 out of top 10 points of interest in this area
While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.
Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Sep 22 to Sep 23
CA $204
CA $239 total
Sep 22 - Sep 23
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from Sep 14 to Sep 15
CA $245
CA $288 total
Sep 14 - Sep 15
includes taxes & fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Sep 22 to Sep 23
CA $230
CA $270 total
Sep 22 - Sep 23
includes taxes & fees
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 Southwest Side
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Southwest Side
Wendella's 90-min Chicago River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
CA $62
per adult
96% of travellers recommend
Other vacations you might like
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Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
