Jackson Park Highlands Holidays
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- Hotel Felix River North/Magnificent Mile
Jul 14 - Jul 26Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago12 nights8.2/10 - Very good (2,778 reviews)"Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable."Reviewed June 8, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stopsNZ$7,339NZ$5,025found 1 day agoper traveller - Level Chicago Fulton Market
Jul 14 - Jul 26Level Chicago Fulton Market + Flight
Downtown Chicago12 nights9.2/10 - Wonderful (493 reviews)"Fully equipmet"Reviewed June 2, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stops - LondonHouse Chicago, Curio Collection by Hilton
Jul 14 - Jul 26LondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago12 nights9.4/10 - Exceptional (3,730 reviews)"We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."Reviewed June 7, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stops - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jul 14 - Jul 26Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago12 nights9.4/10 - Exceptional (2,535 reviews)"This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."Reviewed June 8, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stops - Omni Chicago Hotel
Jul 14 - Jul 26Omni Chicago Hotel + Flight
Downtown Chicago12 nights9.2/10 - Wonderful (1,799 reviews)"Best hotel in Chicago for the price. Perfect location. The staff was very friendly. The rooms are stylish and spacious. One minor inconvenience is that they do not offer room service but I was able to put an order in at the restaurant and pick up was fast and easy."Reviewed June 9, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stopsNZ$7,911NZ$5,558found 1 day agoper traveller
Our guide on 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.
Our pick of the best Jackson Park Highlands Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$278 per night from 29 June to 30 June
NZ$278
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,232 reviews)
"The rooms were spacious and clean. Our room was not difficult to find. The building is old but historic. The place was well maintained and the staff were very helpful. Housekeeping only comes every other day unless requested. It worked for us. I would stay here again."
Reviewed on 9 June 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
The price is NZ$327 per night from 1 July to 2 July
NZ$327
1 July - 2 July
includes taxes & fees
7.8/10 Good! (1,549 reviews)
"The hotel was amazing, the room was clean and big, the only bad thing was the check in… your employees are rude and disgusting… The girl from the breakfast and the guy from the rooftop were nice and respectful, we really like them"
Reviewed on 9 June 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$337 per night from 29 June to 30 June
NZ$337
29 June - 30 June
includes taxes & fees
8.2/10 Very Good! (1,578 reviews)
"Valet was a mess"
Reviewed on 9 June 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
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
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
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
Activities
Chicago Sightseeing River and Lake Cruise
NZ$78
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.