Rolling Meadows Vacation Packages

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Your Rolling Meadows Vacation

Prepare to experience Rolling Meadows on your own terms with a custom Rolling Meadows vacation package! Discovering the best parts of this captivating city is simple with a base in a neighborhood such as Medinah, which is great for golfing, among other things. Woodfield Mall, Schaumburg Medieval Times and LEGOLAND® Discovery Center are just some of the sights you'll want to check out during your trip to Rolling Meadows. Your dream Rolling Meadows vacation is just a few clicks away. Explore hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.

Top Rolling Meadows Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,415, price is now CA $828 per person
CA $828
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly

Reviewed on Aug. 29, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $4,139, price is now CA $2,373 per person
CA $2,373
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,824, price is now CA $1,643 per person
CA $1,643
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug. 29, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,012, price is now CA $1,767 per person
CA $1,767
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,883, price is now CA $1,120 per person
CA $1,120
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

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Rolling Meadows Hotel Deals

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
The price is CA $209 per night from Sep 20 to Sep 21
CA $209
CA $245 total
Sep 20 - Sep 21
includes taxes & fees
Marriott Chicago O'Hare
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 $246 per night from Sep 20 to Sep 21
CA $246
CA $289 total
Sep 20 - Sep 21
includes taxes & fees
Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 13 to Sep 14
CA $197
CA $224 total
Sep 13 - Sep 14
includes taxes & fees
Hyatt Regency O'Hare Chicago
See all 2,216 properties in Rolling Meadows
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
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Discover the most popular places to visit in Rolling Meadows

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 Rolling Meadows

River tour boat in Chicago

Architecture River Tour

CA $57
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 $56
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 Rolling Meadows
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.