Pistakee Highlands Vacations from $484

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Your Pistakee Highlands Vacation

Reserve a Pistakee Highlands vacation package that has everything you need and no unnecessary extras. Great for fishing, walking and camping, consider staying in the neighborhood of Camp Lake. If your trip to Pistakee Highlands includes a little sightseeing, drop by well-known attractions like Volo Auto Museum, Petersen Park Beach and McCullom Lake. Stop dreaming and start doing. Browse the wide range of options on Expedia today and finally put your Pistakee Highlands vacation plans into action!

The Latest Pistakee Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • An outdoor seating area with a glass table, orange cushions, and potted plants.
    Dec 20 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,875 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,496
    $484
    per traveler
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Dec 28 - Jan 1

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (5,647 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,085
    $722
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Dec 28 - Jan 1

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $931
    $631
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • A couple dining at a table with a view of a cityscape and a sunset.
    Dec 10 - Dec 13

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "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..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $1,826
    $1,237
    per traveler
    found 10 hours ago
    Park Hyatt Chicago
  • A modern kitchen with a large island, bar stools, and a city view.
    Jan 22 - Jan 25

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (558 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $733
    $498
    per traveler
    found 1 day ago
    Level Chicago – Old Town
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.