Rosemont Vacation Packages
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Your Rosemont Vacation
Entertainment, history, art and more … There's so much to experience with a Rosemont vacation package. And with the ability to easily customize your city adventure, you know it'll be one that's tough to forget. Eager to explore your new surroundings? Allstate Arena, Rosemont Theatre and Fashion Outlets of Chicago are some of the best places to visit during a trip to Rosemont. Check out Expedia's extensive range of travel options and start planning your ultimate vacation to Rosemont now.
Top Rosemont Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,388, price is now CA $874 per person
CA $874
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on Apr 24, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $2,127, price is now CA $1,251 per person
CA $1,251
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.4/10 Very Good! (1,891 reviews)
The HVAC was annoying AF. It would go on and blow cold air for 10 minutes, then be off for 15-20 minutes repeatedly. It is so loud, it kept waking me up through out the night. As a short person, I did not like the fact the bed was a challenge to get on top. Not everyone is five feet tall.
Reviewed on Apr 26, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,399, price is now CA $879 per person
CA $879
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.
Reviewed on Apr 27, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,713, price is now CA $1,106 per person
CA $1,106
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place
Reviewed on Apr 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,813, price is now CA $1,183 per person
CA $1,183
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Great week-long stay. We loved the king corner room - the views were fantastic. Room was large and comfortable. All staff were really accommodating.
Reviewed on Apr 29, 2026
Rosemont Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from May 26 to May 27
CA $208
CA $237 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (2,513 reviews)
Breakfast buffet was only option
Reviewed on Apr 29, 2026
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2 Rosemont IL
Fully refundable
The price is CA $163 per night from May 25 to May 26
CA $163
CA $188 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (2,925 reviews)
Very clean great staff good food.
Reviewed on Apr 30, 2026
Embassy Suites by Hilton Chicago O'Hare Rosemont
5500 N River Rd Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from May 26 to May 27
CA $195
CA $223 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (1,351 reviews)
Manager didn’t keep his word in refunding money to me for items taken from my room by cleaning staff. Front desk Staff was not helpful or knowledgeable and a housekeeping work went through my suitcase and removed items that didn’t belong to them. I felt my privacy was totally violated. I advise future ...
Reviewed on Apr 29, 2026
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.
Discover the most popular places to visit in Rosemont
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Rosemont
Skydeck - Willis Tower Admission
CA $61
per adult
96% of travellers recommend
Explore a world of travel with Expedia
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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.
