Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Downtown
per person
Feb 26 - Feb 28
found 8 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
Red Roof Inn PLUS+ Chicago - Willowbrook
per person
Mar 7 - Mar 11
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Willowbrook Community Park and Burr Ridge Village Center are located nearby.
Chinatown Hotel Chicago
per person
Mar 7 - Mar 11
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the property condition in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
per person
Mar 7 - Mar 11
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this hotel in Arlington Heights. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Woodfield Mall and Heritage Park are located nearby.
21c Museum Hotel Chicago
per person
Mar 29 - Apr 1
found 4 hours ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
Stay at this 4-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 Millennium Park are located nearby.
Super 8 by Wyndham Crystal Lake
per person
Mar 7 - Mar 11
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly motel in Crystal Lake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Crystal Court Shopping Center and North Wall Rock Climbing are located nearby.
Chicago Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chicago Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Feb 25 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 3 days ago
$58
Roundtrip
found 3 days ago
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 4 days ago
$63
Roundtrip
found 4 days ago
Wed, Feb 19 - Tue, Feb 25
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$68 Roundtrip, found 20 hours ago
$68
Roundtrip
found 20 hours ago
Tue, Feb 18 - Wed, Feb 19
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 21 hours ago
$68
Roundtrip
found 21 hours ago
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