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Highland Hills Vacations from $396

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The Latest Highland Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Oct 4 - Oct 7

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very Good (2,878 reviews)
    "GreatGreat quite wonderful"
    Reviewed July 30, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $627
    $396
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Front of property
    Oct 4 - Oct 7

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (4,872 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $882
    $503
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Lounge
    Oct 4 - Oct 7

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,152 reviews)
    "The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District."
    Reviewed July 28, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,125
    $735
    per traveler
    found 1 day ago
    Pendry Chicago
  • Terrace/patio
    Oct 4 - Oct 7

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,619 reviews)
    "Just stayed one night. Beautiful room view of lake. Front desk staff was welcoming."
    Reviewed July 30, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $748
    $493
    per traveler
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Premium bedding, pillowtop beds, in-room safe, desk
    Oct 15 - Oct 19

    Level Chicago - River North + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,043 reviews)
    "This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities"
    Reviewed July 30, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,149
    $777
    per traveler
    found 1 day ago
    Level Chicago - River North

Highland Hills Hotel Deals

Lobby

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard
2.5 star property
Highland Hills
9.0 out of 10, Wonderful, (2,915 reviews)
$92 nightly
The price is $103
Aug 29 - Aug 30
Total with taxes and fees
SureStay Plus Hotel by Best Western Chicago Lombard
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.
See all properties in Highland Hills
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.