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Chicago Vacations

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Top Holiday Package Deals in Chicago

The Langham, Chicago
The Langham, Chicago
5 out of 5
River North
CA $1,390
CA $1,112
per personAug 19 - Aug 24
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
4.9/5Exceptional! (1,232 reviews)

"Great location. One of the nicest hotels in Chicago.…"

Reviewed on Mar. 15, 2020

Hotel Lincoln
Hotel Lincoln
4 out of 5
Old Town Triangle
CA $892
CA $797
per personAug 19 - Aug 24
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
4.3/5Excellent! (2,218 reviews)

"Great room, customer service and bikes! Rob the manager was terrific and responsive to our needs.…"

Reviewed on Jun. 28, 2020

W Chicago - City Center
W Chicago - City Center
4 out of 5
The Loop
CA $1,014
CA $923
per personAug 19 - Aug 24
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
3.9/5Good! (999 reviews)

"Love the fitness center plus my room. Very clean ans spacious.…"

Reviewed on Dec. 1, 2019

DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
3.5 out of 5
Streeterville
CA $794
CA $780
per personAug 19 - Aug 24
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
4.2/5Very Good! (5,709 reviews)

"Easy check in, clean rooms, great location, I’ll definitely be back.…"

Reviewed on Mar. 8, 2020

Hilton Chicago
Hilton Chicago
4 out of 5
The Loop
CA $886
CA $875
per personAug 19 - Aug 24
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
4.2/5Very Good! (6,079 reviews)

"We will be back! I booked the trip for my sons 15th birthday. When we got there we got a room upgrade. Everyone was so nice and helpful. Our second day everything closed because of coronavirus, the consierge was so helpful giving us ideas on other things to do! My only negative would be I wish the pool would have stayed open past 8 since there was nothing to do in the city.…"

Reviewed on Mar. 17, 2020

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Discover neighborhoods in Chicago

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Top Hotels in Chicago

Estimated price for 1 night / 2 adults
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5
85 East Wacker Drive, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is CA $133 per night
4.6/5Exceptional! (2,331 reviews)

"I love London house very nice luxury hotel. Would Recommend"…"

Reviewed on Jul. 4, 2020

LondonHouse Chicago, Curio Collection by Hilton
The Godfrey Hotel Chicago
The Godfrey Hotel Chicago
4.5 out of 5
127 West Huron, at LaSalle, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is CA $174 per night
4.3/5Excellent! (1,621 reviews)

"Overall pleasing experience, I would not recommend you bring children if you have them even though they say all are welcome. Great traveling distance to downtown attractions. Great views of the sky line. The rooftop is bar far one of my favorites in the city. Would recommend will travel back there ..."…"

Reviewed on Jul. 1, 2020

The Godfrey Hotel Chicago
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
4.5 out of 5
20 E Chestnut St, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is CA $256 per night
4.6/5Exceptional! (2,694 reviews)

"The view we had was beautiful. Very well kept and clean."…"

Reviewed on Jun. 27, 2020

Sofitel Chicago Magnificent Mile

Top things to do in Chicago

Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions
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Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

CA $112
Per adult
80% of travellers recommend
Architecture River Tour from Navy Pier
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Architecture River Tour from Navy Pier

CA $67
Per adult
94% of travellers recommend
Chicago CityPASS: Admission to Top 5 Chicago Attractions
Image for Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS: Admission to Top 5 Chicago Attractions

CA $148
Per adult
94% of travellers recommend