Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Zion by IHG
Save 100% on your flight
Price was $312, price is now $204 per person
$204
per person
Jul 3 - Jul 5
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Zion. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Carmel Park and Ophir Park are located nearby.
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,445, price is now $813 per person
$813
per person
Jul 4 - Jul 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $943, price is now $556 per person
$556
per person
Jun 25 - Jun 28
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 $1,518, price is now $908 per person
$908
per person
Jul 4 - Jul 10
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.
Eurostars Magnificent Mile
Save 100% on your flight
Price was $1,152, price is now $702 per person
$702
per person
Jun 3 - Jun 7
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.
Level Chicago – Old Town
Save 100% on your flight
Price was $855, price is now $528 per person
$528
per person
Jun 26 - Jun 29
found 11 hours 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
Save 100% on your flight
Price was $638, price is now $397 per person
$397
per person
Jun 26 - Jun 29
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.
Le Méridien Essex Chicago
Save 100% on your flight
Price was $853, price is now $532 per person
$532
per person
Jun 26 - Jun 29
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field 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, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 7 hours ago
$76
Roundtrip
found 7 hours ago
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$78 Roundtrip, found 7 hours ago
$78
Roundtrip
found 7 hours ago
Tue, Jun 2 - Wed, Jun 3
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$93 Roundtrip, found 4 days ago
$93
Roundtrip
found 4 days ago
Mon, Jun 29 - Sat, Jul 11
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
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