Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Dorothy's
Price was $698, price is now $496 per person
$496
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this B&B in Chicago. Enjoy free breakfast, free WiFi, and housekeeping. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Swissotel - Chicago
Save 100% on your flight
Price was $1,020, price is now $678 per person
$678
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,086, price is now $728 per person
$728
per person
Jul 10 - Jul 13
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,244, price is now $852 per person
$852
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Urban Chicago Oasis
Save 100% on your flight
Price was $1,308, price is now $909 per person
$909
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and balconies or patios. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,419, price is now $995 per person
$995
per person
Jul 10 - Jul 13
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 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.
Pendry Chicago
Save 100% on your flight
Price was $1,220, price is now $862 per person
$862
per person
Jul 23 - Jul 26
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 rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
La Banque Hotel
Price was $773, price is now $550 per person
$550
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Tue, Jul 21 - Sat, Jul 25
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$142 Roundtrip, found 16 hours ago
$142
Roundtrip
found 16 hours ago
Sat, Jun 13 - Wed, Jun 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 16 hours ago
$152
Roundtrip
found 16 hours ago
Sat, Jul 4 - Wed, Jul 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 11 hours ago
$164
Roundtrip
found 11 hours ago
Mon, Aug 17 - Thu, Aug 20
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
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