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Highland Hills Vacations from $466

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The Latest Highland Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Bar (on property)
    Sep 25 - Sep 28

    The Whitehall Hotel, BW Premier Collection + Flight

    Downtown Chicago
    3 nights
    3.5 star property
    8.4/10 - Very Good (3,935 reviews)
    "Clean room, good location"
    Reviewed July 20, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $736
    $466
    per traveler
    found 2 days ago
    The Whitehall Hotel, BW Premier Collection
  • Full-size fridge, microwave, oven, stovetop
    Sep 30 - Oct 5

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (504 reviews)
    "Good"
    Reviewed July 20, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,517
    $918
    per traveler
    found 2 days ago
    Level Chicago – Old Town
  • Front of property
    Sep 25 - Sep 28

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (4,756 reviews)
    "Big rooms, nice lobby, and great breakfast. Good location and easy check in."
    Reviewed July 20, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,006
    $635
    per traveler
    found 2 days ago
    Hotel Riu Plaza Chicago
  • Lobby sitting area
    Aug 22 - Aug 28

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    8.4/10 - Very Good (2,047 reviews)
    "The staff was amazing! They were very friendly and helpful. The hotel itself was great and in a great area, but it is older and the rooms are a little small. I was not claustrophobic or anything like that. We stayed in the king size bed room and it was perfect for 2 people but any more than that would have been tight. Overall, the staff was very friendly, the rooms and lobby were clean, and it was the perfect distance away from everything we wanted to do."
    Reviewed July 20, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,327
    $850
    per traveler
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Indoor wedding
    Sep 25 - Sep 28

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,502 reviews)
    "Good and easy service"
    Reviewed July 20, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $899
    $589
    per traveler
    found 2 days ago
    Swissotel - Chicago

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, (2,894 reviews)
$97 nightly
The price is $107
Aug 3 - Aug 4
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.