Medinah Vacation Packages

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Your Medinah Vacation

Entertainment, history, art and more … There's so much to immerse yourself in with a Medinah vacation package. And with the ability to easily customize your city adventure, you know it'll be one you won't forget. If your trip to Medinah includes a little sightseeing, visit major attractions such as Woodfield Mall, Schaumburg Medieval Times and LEGOLAND® Discovery Center. A couple of clicks is all it takes to put together a customized Medinah vacation on Expedia.

Top Medinah Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $988, price is now CA $727 per person
CA $727
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $2,254, price is now CA $1,466 per person
CA $1,466
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,348, price is now CA $916 per person
CA $916
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10

Reviewed on Feb 9, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,560, price is now CA $1,140 per person
CA $1,140
per person
Apr 16 - Apr 21
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Amazing hotel. Always stay here when I make a trip to Chicago.

Reviewed on Feb 10, 2026

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,478, price is now CA $1,085 per person
CA $1,085
per person
Apr 16 - Apr 21
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,034 reviews)
All good. bar staff was not that friendlly

Reviewed on Feb 3, 2026

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Medinah Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $266 per night from Mar 7 to Mar 8
CA $266
CA $312 total
Mar 7 - Mar 8
includes taxes & fees
8.2/10 Very Good! (2,215 reviews)
A very good value. A bit worn, great bed but half the price of the Westin Denver airport.

Reviewed on Feb 8, 2026

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Feb 27 to Feb 28
CA $194
CA $228 total
Feb 27 - Feb 28
includes taxes & fees
8.6/10 Excellent! (1,218 reviews)
aa

Reviewed on Feb 5, 2026

Marriott Chicago O'Hare
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd Rosemont IL
Fully refundable
The price is CA $160 per night from Feb 16 to Feb 17
CA $160
CA $182 total
Feb 16 - Feb 17
includes taxes & fees
8.6/10 Excellent! (2,731 reviews)
Very nice

Reviewed on Feb 6, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 2,003 properties in Medinah
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 Medinah

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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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 featuring a sunset and rides

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 Medinah

Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Medinah

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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.