Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $845, price is now $565 per person
$565
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Save 100% on your flight
Price was $1,206, price is now $739 per person
$739
per person
Jul 29 - Aug 1
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,214, price is now $766 per person
$766
per person
Jul 29 - Aug 1
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.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $1,085, price is now $694 per person
$694
per person
Jul 29 - Aug 1
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
Save 100% on your flight
Price was $1,018, price is now $671 per person
$671
per person
Jul 29 - Aug 1
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 $1,645, price is now $1,093 per person
$1,093
per person
Jul 23 - Jul 27
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.
The Langham, Chicago
Save 100% on your flight
Price was $1,135, price is now $761 per person
$761
per person
Aug 31 - Sep 3
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.
Wind Creek Southland Casino and Hotel
Save 100% on your flight
Price was $1,143, price is now $766 per person
$766
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club 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, Sep 29 - Tue, Oct 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Tue, Jul 28 - Wed, Aug 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Sat, Jul 18 - Tue, Jul 21
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Sat, Aug 15 - Thu, Sep 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
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