Skip to main content

Roseland Vacations from $421

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Roseland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Oct 2 - Oct 5

    Holiday Inn Chicago O'Hare – Rosemont by IHG + Flight

    Rosemont
    3 nights
    3.0 star property
    9.0/10 - Wonderful (3,082 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $895
    $421
    per traveler
    found 1 day ago
    Holiday Inn Chicago O'Hare – Rosemont by IHG
  • Front of property
    Sep 24 - Sep 27

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (4,798 reviews)
    "Perfect location,superb breakfast buffet, rooftop bar was outstanding and a great option for happy hour!!! We will definitely stay here again on our next trip to Chicago"
    Reviewed July 24, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,060
    $616
    per traveler
    found 2 days ago
    Hotel Riu Plaza Chicago
  • Lobby
    Sep 3 - Sep 6

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very Good (2,859 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $879
    $561
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Bar (on property)
    Sep 24 - Sep 27

    The Whitehall Hotel, BW Premier Collection + Flight

    Downtown Chicago
    3 nights
    3.5 star property
    8.4/10 - Very Good (3,922 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $806
    $518
    per traveler
    found 2 days ago
    The Whitehall Hotel, BW Premier Collection
  • Indoor wedding
    Sep 24 - Sep 27

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,507 reviews)
    "The fact that the keep their own bees and incorporate their honey into their Food. The cocktails in the lounge and the Hummus platter were amazing. Maria was our Server all weekend, she took extremely good care of us!! Breakfast by room room service was really good and convenient. The one Thing that I didn’t like about room service was there was a two different extra charges. One was a Service Charge and one was a Convenience charge, which, really are one and the same. Seemed completely..."
    Reviewed July 23, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,092
    $709
    per traveler
    found 2 days ago
    Swissotel - Chicago

Discover the most popular places to visit in Roseland

Abbott Park

Abbott Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.