Summit Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Summit Vacation
Book a customized Summit vacation package that has only the things you need and nothing you don't. Great for cafes, shopping and history, think about basing yourself in the neighborhood of Magnificent Mile. If your trip to Summit includes some sightseeing, hit up famous attractions like Brookfield Zoo, SeatGeek Stadium and Chicago Ridge Shopping Mall. Don't put off exploring this city any longer. The perfect Summit vacation is a few quick clicks away with Expedia.
Top Summit Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,169, price is now CA $881 per person
CA $881
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,941 reviews)
Hotel is in a great location! We were on the top floor and we had no issues with the elevator, despite it being down the first day. Room was clean and beds were comfortable. AC is loud so if you are a light sleeper like I am, bring ear plugs. I would definitely stay here again.
Reviewed on May 30, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,682, price is now CA $1,045 per person
CA $1,045
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Price was CA $3,834, price is now CA $2,821 per person
CA $2,821
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (142 reviews)
My wife and I really enjoyed our stay at this location. The accommodations were very nice. However, what really stuck out was the hotel staff, its the best that we have experienced.
Reviewed on Sep 5, 2025
Hilton Chicago
Downtown Chicago
Price was CA $1,503, price is now CA $1,126 per person
CA $1,126
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.6/10 Excellent! (2,813 reviews)
The fitness gym, games, elevators, Grab n Go facilities were all very good. The reception desk was unfriendly and gave false info. Housekeeping was also lacking.
Reviewed on May 30, 2026
Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
Price was CA $2,421, price is now CA $1,840 per person
CA $1,840
per person
Aug 2 - Aug 8
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,343 reviews)
We had the best stay here! Within a short walk to the trains ($10 for 2 of us to jump in and off as many times as we wanted in 24 hours) to get down town, super comfy room and beautiful views into the city! Valet was top notch and worth every penny! All staff were so friendly and helpful! Breakfast was delicious and a great start to a day of walking and shopping. Would totally stay here again and stay longer - such a great start and finish to our trip!
Reviewed on May 26, 2026
Summit Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,135 reviews)
"The room was small and was missing modern convinces-microwave-better seating space. The staff were friendly and the restaurant was great! I only wished we had gotten a better room! Special shout out to Steve P. the doorman for his service and friendly demeanor!!"
Reviewed on May 30, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Jun 30 to Jul 1
CA $261
CA $349 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,301 reviews)
"Clean"
Reviewed on May 31, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $210 per night from Jun 14 to Jun 15
CA $210
CA $249 total
Jun 14 - Jun 15
includes taxes & fees
7.8/10 Good! (1,494 reviews)
"Great location for shopping. Well maintained, slightly dated rooms."
Reviewed on May 31, 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 Summit
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Michigan Avenue
4.5/5(20 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.
What to do in Summit
Skydeck - Willis Tower Admission
CA $60
per adult
96% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
