Whether you call it the Windy City, Pie Town, or the Hub of the Midwest, you'll find great deals to Chicago!
| Flight + Hotel* | Hotel Only** | |
Featured Property
Area: Loop/ Magnificent Mile/ River North
This luxury boutique hotel near the Magnificent Mile offers modern residential comfort and classic hospitality.
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$430 per person
Save 24%
May
18 -23
includes flight + 5 nights hotel, taxes & fees
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$169 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
The Hard Rock Hotel Chicago offers a unique blend of classic architecture, contemporary style, and unparalleled...
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$418 per person
Save 17%
May
18 -23
includes flight + 5 nights hotel, taxes & fees
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$129 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
Club Quarters is an exclusive and club-like hotel that ensures privacy and tranquility.
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$308 per person
Save 15%
May
18 -23
includes flight + 5 nights hotel, taxes & fees
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$63 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
Tremont is home to Mike Ditka's with two floors of fine dining and Mike's prized collection of sports memorabilia....
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$368 per person
Save 15%
Jun
17 -22
includes flight + 5 nights hotel, taxes & fees
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$79 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
Experience peace and calm in a members-only, club-like atmosphere in Chicago's Central Loop.
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$299 per person
Save 14%
May
18 -23
includes flight + 5 nights hotel, taxes & fees
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$63 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
The River Hotel is located in the center of downtown Chicago, overlooking the famous Chicago River, Tribune Tower...
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$311 per person
Save 14%
May
18 -23
includes flight + 5 nights hotel, taxes & fees
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$63 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
The pride of Chicago, The Drake has been the choice of celebrities and heads of state since its opening in 1920.
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$440 per person
Save 13%
Jun
17 -22
includes flight + 5 nights hotel, taxes & fees
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$111 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
The Westin is a retreat offering a full spectrum of services that provide everything from tranquility to...
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$483 per person
Save 12%
May
18 -23
includes flight + 5 nights hotel, taxes & fees
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$109 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
As one of the first high-rises to grace fashionable Michigan Avenue, Allerton became synonymous with high style.
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$406 per person
Save 11%
May
18 -23
includes flight + 5 nights hotel, taxes & fees
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$115 per night
includes hotel only, excludes taxes and fees
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Area: Loop/ Magnificent Mile/ River North
The Omni Chicago Hotel is located approximately 17 miles from Chicago's O'Hare International Airport in the heart...
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$487 per person
Save 10%
May
18 -23
includes flight + 5 nights hotel, taxes & fees
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$161 per night
includes hotel only, excludes taxes and fees
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