Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Save 100% on your flight
Price was $514, price is now $320 per person
$320
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a 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.

The Emily Hotel
Price was $1,752, price is now $862 per person
$862
per person
Nov 10 - Nov 16
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 United Center and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago
Price was $2,180, price is now $1,157 per person
$1,157
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

The Langham, Chicago
Price was $3,789, price is now $2,161 per person
$2,161
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $626, price is now $358 per person
$358
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Chicago Athletic Association, a Hyatt Hotel
Save 100% on your flight
Price was $1,030, price is now $596 per person
$596
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Arlo Chicago
Save 100% on your flight
Price was $835, price is now $504 per person
$504
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

La Banque Hotel
Save 100% on your flight
Price was $551, price is now $334 per person
$334
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
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, Sep 24 - Wed, Oct 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$84 Roundtrip, found 1 day ago
$84
Roundtrip
found 1 day ago

Sat, Sep 6 - Wed, Sep 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago

Sat, Sep 27 - Wed, Oct 1
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 5 days ago
$100
Roundtrip
found 5 days ago

Tue, Oct 28 - Tue, Nov 4
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
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