Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $515, price is now $331 per person
$331
per person
May 8 - May 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
La Banque Hotel
Save 100% on your flight
Price was $637, price is now $373 per person
$373
per person
May 1 - May 4
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.
JW Marriott Chicago
Save 100% on your flight
Price was $651, price is now $419 per person
$419
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Viceroy Chicago
Save 100% on your flight
Price was $1,063, price is now $715 per person
$715
per person
Apr 22 - Apr 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, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Save 100% on your flight
Price was $854, price is now $589 per person
$589
per person
Apr 3 - Apr 8
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.
Illinois Beach Hotel
Price was $511, price is now $361 per person
$361
per person
Mar 17 - Mar 22
found 1 day 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.
InterContinental Chicago Magnificent Mile by IHG
Save 100% on your flight
Price was $856, price is now $608 per person
$608
per person
Apr 26 - Apr 30
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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, May 12 - Sat, May 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 13 hours ago
$56
Roundtrip
found 13 hours ago
Mon, Apr 27 - Tue, May 12
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 7 hours ago
$56
Roundtrip
found 7 hours ago
Wed, Mar 11 - Wed, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$57 Roundtrip, found 16 hours ago
$57
Roundtrip
found 16 hours ago
Mon, Mar 9 - Tue, Mar 10
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$57 Roundtrip, found 18 hours ago
$57
Roundtrip
found 18 hours ago
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