Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Super Sleep Inn By OYO I-80 Princeton
Save 100% on your flight
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Swissotel - Chicago
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Palmer House a Hilton Hotel
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
La Banque Hotel
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
The Hoxton Chicago
Save 100% on your flight
per person
Aug 28 - Sep 3
found 7 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Radisson Blu Aqua Hotel Chicago
Save 100% on your flight
per person
Aug 28 - Sep 3
found 7 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Chicago/Magnificent Mile Suites
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 7 hours ago
$90
Roundtrip
found 7 hours ago
Tue, Jul 8 - Tue, Jul 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 5 hours ago
$97
Roundtrip
found 5 hours ago
Thu, Jun 26 - Sat, Jun 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Tue, Jul 22 - Wed, Jul 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$109 Roundtrip, found 5 hours ago
$109
Roundtrip
found 5 hours ago
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