Jackson Park Highlands Vacation Packages
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Top Holiday Package Deals in Jackson Park Highlands
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,359, price is now CA $957 per person
CA $957
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.
Reviewed on May 7, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,447, price is now CA $962 per person
CA $962
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,683, price is now CA $1,142 per person
CA $1,142
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again
Reviewed on May 6, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,626, price is now CA $1,148 per person
CA $1,148
per person
Jun 30 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Where to stay in Jackson Park Highlands
Find the best Jackson Park Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Jackson Park Highlands
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Jackson Park Highlands Hotel Deals
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 20 to May 21
CA $118
CA $182 total
May 20 - May 21
includes taxes & fees
8.2/10 Very Good! (2,691 reviews)
The room was a little small, but fit my needs on a 3 day business trip. The bar downstairs served a limited breakfast... And had free fruit, and Coffee in the morning. The staff was extremely friendly, and very attentive to guests. In summary I would stay here again on business.
Reviewed on May 7, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from May 25 to May 26
CA $196
CA $233 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,182 reviews)
Everything was good. Nothing to complain
Reviewed on May 8, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from May 27 to May 28
CA $204
CA $281 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,086 reviews)
The hotel was so clean and everyone was friendly! Great location!
Reviewed on May 7, 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.
Frequently asked questions
Discover the most popular places to visit in Jackson Park Highlands
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
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
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
CA $61
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.