Summit Vacation Packages

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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $851, price is now CA $543 per person
CA $543
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,007 reviews)
This was by far the BEST Hotel!!!

Reviewed on Sep. 1, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) 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

Art Villa

Art Villa

5 out of 5
West Town
Price was CA $4,082, price is now CA $2,538 per person
CA $2,538
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,445, price is now CA $931 per person
CA $931
per person
Oct 16 - Oct 19
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

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 out of 5
Chinatown
Price was CA $2,193, price is now CA $1,419 per person
CA $1,419
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (982 reviews)
Parking was pretty weird and inconvenient. It all worked out, but it was ambiguous and unsure the whole time. It could have just as easily been a nightmare if it was just the tiniest bit busier.

Reviewed on Sep. 3, 2025

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Summit Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Sep 4 to Sep 5
CA $176
CA $207 total
Sep 4 - Sep 5
includes taxes & fees
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Sep 22 to Sep 23
CA $252
CA $296 total
Sep 22 - Sep 23
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
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
The Wade
See all 5,114 properties in Summit
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Summit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

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.

Michigan Avenue
Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Summit

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Summit
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.