Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
Save 100% on your flight
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby.
InterContinental Chicago Magnificent Mile by IHG
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago O'Hare Airport
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Swissotel - Chicago
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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 Michigan Avenue are located nearby.
Staybridge Suites Chicago - Glenview by IHG
Save 100% on your flight
per person
Jun 13 - Jun 18
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 3-star golf hotel in Glenview. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kohl Children's Museum and Glenview Prairie Golf Club are located nearby.
Congress Plaza Hotel
Save 100% on your flight
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Soldier Field are located nearby.
Hilton Garden Inn Chicago North Shore/Evanston
Save 100% on your flight
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Aragon Ballroom and Riviera Theatre are located nearby.
Embassy Suites by Hilton Chicago Schaumburg Woodfield
Save 100% on your flight
per person
Jun 13 - Jun 18
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center 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 - Tue, Jun 24
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$68 Roundtrip, found 5 days ago
$68
Roundtrip
found 5 days ago
Wed, Jun 18 - Wed, Jun 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Tue, Aug 5 - Wed, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Thu, Apr 24 - Tue, Apr 29
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$94 Roundtrip, found 14 hours ago
$94
Roundtrip
found 14 hours ago
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