Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Save 100% on your flight
per person
Jul 13 - Jul 16
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Virgin Hotels Chicago
Save 100% on your flight
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town
Save 100% on your flight
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Harrah's Joliet Casino & Hotel
Save 100% on your flight
per person
Jul 22 - Jul 26
found 23 hours ago
Roundtrip flight included
New Orleans (MSY) to Chicago (CHI)
Stay at this 3.5-star business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harrah's Casino and Route 66 Raceway are located nearby.
Kimpton Gray Hotel by IHG
Save 100% on your flight
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Institute of Chicago and Chicago Riverwalk are located nearby.
InterContinental Chicago Magnificent Mile by IHG
Save 100% on your flight
per person
Jul 13 - Jul 16
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.
La Banque Hotel
Save 100% on your flight
per person
Jun 25 - Jun 29
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Fri, May 30 - Mon, Jun 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$62 Roundtrip, found 15 hours ago
$62
Roundtrip
found 15 hours ago
Wed, May 14 - Tue, May 20
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$75 Roundtrip, found 2 days ago
$75
Roundtrip
found 2 days ago
Wed, May 28 - Tue, Jun 3
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Tue, May 27 - Tue, Jun 3
LGA
LaGuardia
ORD
O'Hare Intl.
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
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