Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Michigan Avenue are located nearby.
Baymont by Wyndham Gurnee
per person
Apr 10 - Apr 14
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Six Flags Great America and Great Wolf Lodge Water Park are located nearby.
L7 Chicago by LOTTE
Save 100% on your flight
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Chicago Getaway Hostel
per person
Apr 10 - Apr 14
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this hostel in Chicago. Enjoy parking (surcharge), a 24-hour front desk, and a business center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Super 8 by Wyndham Crystal Lake
per person
Mar 7 - Mar 11
found 1 day 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.
Ambassador Chicago, part of JdV by Hyatt
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Navy Pier are located nearby.
Embassy Suites by Hilton Chicago Naperville
per person
Apr 10 - Apr 14
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Nike Sports Complex are located nearby.
Hilton Chicago
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Michigan Avenue 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, Feb 26 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 9 hours ago
$58
Roundtrip
found 9 hours ago
Wed, Feb 19 - Tue, Feb 25
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Wed, Feb 12 - Wed, Feb 19
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
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