Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream
Save 100% on your flight
per person
Jun 8 - Jun 13
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 Cosley Zoo and Dupage County Historical Museum are located nearby.
Cambria Hotel Chicago Loop - Theatre District
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
La Banque Hotel
Save 100% on your flight
per person
May 29 - Jun 3
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Four Points by Sheraton Chicago O'Hare Airport
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Hilton Garden Inn Chicago Downtown South Loop
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 4-star 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.
Pendry Chicago
per person
May 25 - May 28
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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 Chicago Riverwalk and Millennium Park 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, Jun 17 - Wed, Jun 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Sat, Apr 26 - Wed, Apr 30
LGA
LaGuardia
ORD
O'Hare Intl.
$81 Roundtrip, found 4 days ago
$81
Roundtrip
found 4 days ago
Sun, May 4 - Thu, May 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 3 days ago
$83
Roundtrip
found 3 days ago
Wed, May 14 - Tue, May 20
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$84 Roundtrip, found 12 hours ago
$84
Roundtrip
found 12 hours ago
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