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From Chicago
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Weekend getaways Leave on Saturday and come back on Monday · final price when you tap

Las VegasSat, Oct 24 to Mon, Oct 26
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New OrleansSat, Oct 24 to Mon, Oct 26
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NashvilleSat, Oct 24 to Mon, Oct 26
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Featured staysTotal price with taxes

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citizenM Miami WorldcenterFree cancellation
citizenM Miami Worldcenter
8.9· Miami
7 nights, 2 guests from$1,258.97
citizenM Miami BrickellFree cancellation
citizenM Miami Brickell
8.7· Miami
7 nights, 2 guests from$1,332.48
Motto by Hilton New York City Chelsea
Motto by Hilton New York City Chelsea
10.0· New York
7 nights, 2 guests from$1,954.61
Hilton Garden Inn NYC Financial Center/Manhattan DowntownFree cancellation
Hilton Garden Inn NYC Financial Center/Manhattan Downtown
9.2· New York
7 nights, 2 guests from$2,175

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5 days / 4 nights
Miami
Jan 14 to 18 · from ChicagoFlight and hotel at today’s price, taxes included.See flight + hotel
6 days / 5 nights
Orlando
Apr 10 to 15 · from ChicagoFlight and hotel at today’s price, taxes included.See flight + hotel
5 days / 4 nights
New York
May 6 to 10 · from ChicagoFlight and hotel at today’s price, taxes included.See flight + hotel
8 days / 7 nights
Madrid
Apr 21 to 28 · from ChicagoFlight and hotel at today’s price, taxes included.See flight + hotel