Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
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Courtyard by Marriott Chicago Magnificent Mile
Save 100% on your flight
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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Pendry Chicago
Save 100% on your flight
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
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Kinzie Hotel
Save 100% on your flight
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Chicago Theatre are located nearby.
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Hampton Inn Chicago-Carol Stream
Save 100% on your flight
per person
May 12 - May 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this hotel in Carol Stream. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Royal Golf Club at Klein Creek and Xtreme Trampolines are located nearby.
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Super Sleep Inn By OYO I-80 Princeton
Save 100% on your flight
per person
May 12 - May 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this motel in Princeton. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Bureau County Fairgrounds and Soldiers and Sailors Memorial are located nearby.
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The Chicago Hotel Collection - Wrigleyville
Save 100% on your flight
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
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DoubleTree by Hilton Chicago - Oak Brook
Save 100% on your flight
per person
May 12 - May 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Oak Brook. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Oakbrook Center Mall and Drury Lane Theater are located nearby.
Chicago Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
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Chicago Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
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Sat, May 17 - Tue, May 20
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$48 Roundtrip, just found
$48
Roundtrip
just found
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Tue, May 20 - Wed, May 28
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$59 Roundtrip, found 5 days ago
$59
Roundtrip
found 5 days ago
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Tue, Mar 25 - Wed, Apr 2
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$70 Roundtrip, found 4 days ago
$70
Roundtrip
found 4 days ago
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Wed, Mar 26 - Tue, Apr 1
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$70 Roundtrip, found 3 days ago
$70
Roundtrip
found 3 days ago
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