Search Deals onHighland Park Vacation Packages
Highland Park Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Sheraton Grand Chicago Riverwalk
Price was $599, price is now $377 per person
$377
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pendry Chicago
Price was $824, price is now $520 per person
$520
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Beautiful rooms and service.
Reviewed on Nov 5, 2026

Level Chicago Fulton Market
Price was $857, price is now $557 per person
$557
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Weird space w the way the bed is no access off the side and the counter was stained badly. There was a 28$ additional amenity fee that they slapped on upon check in. The pool is closed and didn’t use the weight room it was a one night stay. over priced but could be ok for a long stay w the kitchen
Reviewed on Nov 6, 2026

Hotel Riu Plaza Chicago
Price was $845, price is now $554 per person
$554
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago - River North
Price was $630, price is now $419 per person
$419
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Park Hyatt Chicago
Price was $1,825, price is now $1,236 per person
$1,236
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott.
For example, there was a hair in the bed. When we reported it, the hotel changed the sheets and asked if we wanted to switch rooms, but no apology or other compensation was offered.
The service was fine but incredibly slow, which we experienced with three different requests. Two were for the same bath salts, which are already provided in the room, so it wasn’t a special request. We had to call twice, and they arrived after 45 to 55 minutes. For the third, I went down to the front desk to ask for a printer, and they offered to print the documents and send them to my room. After 45 minutes, I went back down, and it turned out they had completely forgotten about the request, so I had them printed right there.
The pool was dirty. On three different occasions over two days, there were toys left in the pool even after the people using them were already gone. The fruit in the gym was also old and had gone bad.
Reviewed on Nov 4, 2026

The Talbott, Autograph Collection
Price was $742, price is now $504 per person
$504
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Eurostars Magnificent Mile
Price was $552, price is now $377 per person
$377
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The room itself was pretty clean, it had a good shower which is sometimes rare to find. The staff was friendly and housekeeping was responsive. Close to things, but I wouldn’t necessarily say walking distance. It was pretty noisy but hard to get away from that in a city.
Reviewed on Nov 7, 2026
Highland Park Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Highland Park Vacation Packages 5-7 Night Stays
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Dec 4 - Wed, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 5 hours ago
$189
Roundtrip
found 5 hours ago

Tue, Jan 5 - Tue, Jan 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$247 Roundtrip, just found
$247
Roundtrip
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Tue, Nov 10 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,140 Roundtrip, just found
$1,140
Roundtrip
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Sun, Nov 8 - Mon, Feb 1
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$4,382 Roundtrip, just found
$4,382
Roundtrip
just found
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