Search Deals on
Chicago Vacation Packages

Build your package with 2 more options

Chicago Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $686, price is now $460 per person
$460
per person
Jun 23 - Jun 28
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,233, price is now $628 per person
$628
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $1,189, price is now $737 per person
$737
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $851, price is now $536 per person
$536
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,092, price is now $701 per person
$701
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, 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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,506, price is now $1,003 per person
$1,003
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Price was $1,112, price is now $755 per person
$755
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $877, price is now $609 per person
$609
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $851, price is now $536 per person
$536
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,233, price is now $628 per person
$628
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,189, price is now $737 per person
$737
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,092, price is now $701 per person
$701
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Chicago Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $885, price is now $475 per person
$475
per person
Jun 21 - Jun 26
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,438, price is now $712 per person
$712
per person
Jun 21 - Jun 26
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,672, price is now $999 per person
$999
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,436, price is now $864 per person
$864
per person
Jun 3 - Jun 8
found 20 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, Apr 21 - Tue, Apr 28
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 3 days ago
$56
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Apr 21 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Apr 28, priced at $56 found 3 days ago
Spirit Airlines
Thu, Apr 23 - Sat, Apr 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, Apr 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Apr 25, priced at $68 found 1 hour ago
Spirit Airlines
Tue, Apr 28 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $73 found 1 day ago
Frontier Airlines
Wed, Apr 15 - Tue, Apr 21
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Apr 21, priced at $78 found 1 day ago