Jackson Park Highlands Vacations from ￥48,177
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The Latest Jackson Park Highlands Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥74,690, price is now ￥48,177 per person
￥48,177
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
The lobby and common areas are lovely and the room was really small, but fine. Was annoyed by an additional $32/day “destination fee” which they branded as paying for “perks” (like access to the fitness center or coffee in the lobby in the morning) that simply come with other stays in hotels that charge similarly for rooms, including in neighboring downtown Chicago hotels. The most annoying “perk” was a $10 credit that had to be used in the bar or restaurant and when we tried to use with a 10% off discount coupon that was in the room, the already condescending bartender was incredibly dismissive and refused to even look at. In hind sight, I’d rather have just lost the $10 (like we did the day before) than had to experience such an off putting interaction with someone hired to enhance a customer’s stay.
I stay in the loop a few times a year and this is the first place I’ve left with no intention to stay again sometime in the future
Reviewed on Sep 30, 2025
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was ￥111,061, price is now ￥75,466 per person
￥75,466
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
The property was clean and the bed very comfortable. Stayed here on a travel layover -- it was super convenient to the airport. They also have a restaurant that was open late -- very helpful, and the food was pretty good.
Reviewed on Sep 28, 2025
Hilton Orrington / Evanston
Downtown Evanston
Price was ￥78,318, price is now ￥53,499 per person
￥53,499
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
7.6/10 Good! (1,007 reviews)
Two mornings received poor service at breakfast.
King bed in room. Could not open cabinet
Reviewed on Sep 15, 2025
Hilton Rosemont Chicago O'Hare
O'Hare
Save 100% on your flight
Price was ￥166,686, price is now ￥120,004 per person
￥120,004
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.6/10 Excellent! (1,006 reviews)
Close to CTA station. Walkong distance to several restaraunts.
Reviewed on Sep 28, 2025
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
5 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
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."
Reviewed on Sep 25, 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥13,025 per night from Oct 27 to Oct 28
￥13,025
￥22,310 total
Oct 27 - Oct 28
includes taxes & fees
7.8/10 Good! (2,387 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."
Reviewed on Sep 24, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥29,904 per night from Oct 29 to Oct 30
￥29,904
￥35,105 total
Oct 29 - Oct 30
includes taxes & fees
8.4/10 Very Good! (4,998 reviews)
"Lots of food options in the area. If you like to walk, you are close to many shops, Navy Pier, malls and the subway line. The hotel was nice, plenty of food included for breakfast and the happy hour is also nice. Rooms were spacious and everything worked nicely."
Reviewed on Sep 26, 2025
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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Wendella's 90-min Chicago River Architecture Tour
￥6,633
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
￥6,633
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.