Hillside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Your Hillside Vacation
An easy way to experience this vibrant city is with a custom-made Hillside vacation package. Base yourself in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our packages are all about you. Any trip to Hillside needs a well-planned itinerary. Fill yours with major attractions such as Brookfield Zoo, Oakbrook Center Mall and Yorktown Shopping Center. Expedia can help you escape the everyday. Tailor your vacation to Hillside to suit your style of travel, whatever that may be.
Top Hillside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Price was CA $1,084, price is now CA $784 per person
CA $784
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
Clean large room. Friendly helpful staff. Garage parking with covered bridge to hotel and casino. Highly recommend.
Reviewed on Jun 25, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,637, price is now CA $2,438 per person
CA $2,438
per person
Sep 12 - Sep 18
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,771, price is now CA $1,956 per person
CA $1,956
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,573, price is now CA $1,113 per person
CA $1,113
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,743, price is now CA $1,242 per person
CA $1,242
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.
Reviewed on Jun 28, 2026
Hillside 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 30 to Jul 1
CA $194
CA $230 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very good! (10,157 reviews)
"This hotel hasn’t been updated in decades. The staff do the best they can with a very old hotel that needs a significant investment to be nice."
Reviewed on Jun 28, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,832 reviews)
"Best location on Michigan Avenue"
Reviewed on Jun 27, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jul 6 to Jul 7
CA $208
CA $248 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,472 reviews)
"Very Good location & reasonable pricing"
Reviewed on Jun 28, 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.
What to do in Hillside
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
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.
