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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,936, price is now CA $1,280 per person
CA $1,280
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $3,626, price is now CA $1,987 per person
CA $1,987
per person
Jul 28 - Aug 2
found 4 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.
Reviewed on May 16, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,965, price is now CA $1,891 per person
CA $1,891
per person
Jul 28 - Aug 2
found 4 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
I loved it here and will definitely stay again.
Reviewed on May 18, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,410, price is now CA $2,288 per person
CA $2,288
per person
Jul 28 - Aug 2
found 4 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,721 reviews)
Great location with a great view. Walking distance to all attractions and restaurants. The room was spacious and comfy beds
Reviewed on May 18, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $2,379, price is now CA $1,605 per person
CA $1,605
per person
Jul 28 - Aug 2
found 4 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
Staff is excellent. Breakfast was below standards - muffins, fruit, juice, and a couple breakfast sandwiches the staff put in the microwave. I’d pass on the breakfast. Nice location. Rooms were okay - the bed in our room was full of cat scratches.
Reviewed on May 18, 2026
Summit Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,158 reviews)
"The classic style leads to smaller rooms, but its all part of the charm in tgis historic beauty."
Reviewed on May 19, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from May 25 to May 26
CA $194
CA $270 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,184 reviews)
"I couldn’t recommend this hotel enough. The location, the staff, cleanliness and just everything was amazing. You’re walkable to the train station and plenty of buses, but a ton of things to do were nearby and just walk. The staff were so nice and attentive. The breakfast buffet often a great selection. ..."
Reviewed on May 19, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,432 reviews)
"Good location, definitely walkable to a lot of shops and restaurants."
Reviewed on May 18, 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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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.
