Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Regal Inn - Chicago O'Hare Airport
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly motel in Franklin Park. 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 Triton College Botanical Garden and Edge Ice Arena are located nearby.
Fairmont Chicago at Millennium Park
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Courtyard by Marriott Chicago Magnificent Mile
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Admiral Motel By Oyo Chicago I-94
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Chicago Museum of Science and Industry and Abbott Park are located nearby.
Edgebrook Motel
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Milwaukee Avenue and Copernicus Center are located nearby.
L7 Chicago by LOTTE
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this boutique 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 Millennium Park and Michigan Avenue are located nearby.
Best Motel By OYO Chicago I-90
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this property in Chicago. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Chicago Museum of Science and Industry 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.
Wed, Mar 12 - Wed, Mar 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$43 Roundtrip, found 5 days ago
$43
Roundtrip
found 5 days ago
Tue, Mar 11 - Wed, Mar 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$48 Roundtrip, found 5 days ago
$48
Roundtrip
found 5 days ago
Tue, Mar 18 - Tue, Mar 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 3 days ago
$48
Roundtrip
found 3 days ago
Wed, Mar 26 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 4 days ago
$48
Roundtrip
found 4 days ago
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