Hillside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Photo by Joe Farmer
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.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,717, price is now CA $1,289 per person
CA $1,289
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $2,293, price is now CA $1,451 per person
CA $1,451
per person
Jun 4 - Jun 8
found 20 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The rooftop wasn’t open, everything else was great
Reviewed on Mar 24, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,347, price is now CA $1,510 per person
CA $1,510
per person
Jun 4 - Jun 8
found 20 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
This was a nice hotel but some staff made us feel uncomfortable and the rooms had flaws (dirt). I expected better for the money however, I met someone who stayed at Travelodge and their hotel flooded. So, I'd recommend this hotel.
Reviewed on Mar 23, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,970, price is now CA $1,474 per person
CA $1,474
per person
Jun 4 - Jun 8
found 20 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans!
The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too!
The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well!
All and all it’s a wonderful place to experience!!!!🍍
Reviewed on Mar 18, 2026
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Mar 25 to Mar 26
CA $159
CA $187 total
Mar 25 - Mar 26
includes taxes & fees
8/10 Very Good! (10,008 reviews)
The room is cozy and decent
Reviewed on Mar 24, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is CA $181 per night from Apr 6 to Apr 7
CA $181
CA $251 total
Apr 6 - Apr 7
includes taxes & fees
9.4/10 Exceptional! (3,617 reviews)
Great hotel
Reviewed on Mar 24, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is CA $179 per night from Apr 5 to Apr 6
CA $179
CA $210 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (5,786 reviews)
Wonderful stay
Reviewed on Mar 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 Hillside
Wrigley Field
4.5/5(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(19 reviews)
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.
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.
What to do in Hillside
Wendella's 90-min Chicago River Architecture Tour
CA $55
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.
