Search Deals on
Chicago Vacation Packages

Build your package with 2 more options

Chicago Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
per person
Mar 7 - Mar 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90

2 out of 5
Woodlawn
per person
Apr 10 - Apr 14
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Chinatown Hotel Chicago

Chinatown Hotel Chicago

1.5 out of 5
Chinatown
per person
Apr 10 - Apr 14
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Baymont by Wyndham Gurnee

Baymont by Wyndham Gurnee

2.5 out of 5
per person
Apr 10 - Apr 14
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)

Chicago Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
per person
Apr 5 - Apr 10
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Apr 5 - Apr 10
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Apr 5 - Apr 10
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
per person
Apr 5 - Apr 10
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
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
Select Frontier Airlines flight, departing Tue, Feb 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Mar 4, priced at $58 found 3 days ago
Frontier Airlines
Wed, Feb 26 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 4 hours ago
$58
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Feb 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $58 found 4 hours ago
Frontier Airlines
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
Select Frontier Airlines flight, departing Wed, Feb 19 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Feb 25, priced at $68 found 1 day ago
Frontier Airlines
Wed, Feb 19 - Sat, Feb 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 6 hours ago
$68
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Feb 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Feb 22, priced at $68 found 6 hours ago