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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,576, price is now CA $1,125 per person
CA $1,125
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Nice hotel I would stay here again

Reviewed on Apr 15, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,895, price is now CA $1,259 per person
CA $1,259
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included

Reviewed on Apr 12, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,146, price is now CA $1,502 per person
CA $1,502
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The best hotel I've ever stayed in. Please get an iron, please get a microwave. And please don’t charge for every single thing! ❤️

Reviewed on Apr 13, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,642, price is now CA $1,178 per person
CA $1,178
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!

Reviewed on Apr 13, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,578, price is now CA $1,861 per person
CA $1,861
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on Apr 7, 2026

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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 $170 per night from Apr 26 to Apr 27
CA $170
CA $200 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,147 reviews)
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Reviewed on Apr 14, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Apr 26 to Apr 27
CA $164
CA $193 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,123 reviews)
We stayed after seeing Hamilton at CIBC Easter weekend. The hotel was busy, but service was quick and representatives were very friendly. The remodeled pool was great for my 11 year old niece.

Reviewed on Apr 15, 2026

Hilton Chicago/Magnificent Mile Suites
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
The price is CA $191 per night from Apr 26 to Apr 27
CA $191
CA $224 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,839 reviews)
Breakfast was great compared to other hotels. The ac worked so that was good. The tv kept cutting off but i think it was because we were streaming so i wasnt too upset. Great staff!

Reviewed on Apr 15, 2026

Embassy Suites by Hilton Chicago Downtown River North
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.
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Discover the most popular places to visit in Summit

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

What to do in Summit

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Summit

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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.