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Downtown Des Plaines Vacation Packages

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The Latest Downtown Des Plaines Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Sept 17 - Sept 20

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very good (2,843 reviews)
    "Great location, clean room, super quiet hotel, great staff. Definitely recommend!"
    Reviewed July 17, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,466
    CA $938
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Lounge
    Sept 3 - Sept 6

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,150 reviews)
    "Good property but perhaps a bit more modest than reviews"
    Reviewed July 12, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,815
    CA $1,243
    per traveller
    found 1 day ago
    Pendry Chicago
  • Terrace/patio
    Aug 27 - Aug 30

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

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,592 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $2,087
    CA $1,451
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Premium bedding, pillowtop beds, in-room safe, desk
    Sept 17 - Sept 20

    Level Chicago - River North + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,035 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,884
    CA $1,313
    per traveller
    found 1 day ago
    Level Chicago - River North
  • Smart TV
    Sept 24 - Sept 27

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (528 reviews)
    "Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!"
    Reviewed July 17, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,578
    CA $1,111
    per traveller
    found 1 day ago
    Level Chicago Fulton Market