Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Save 100% on your flight
Price was $281, price is now $159 per person
$159
per person
Jan 9 - Jan 11
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 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Art Villa
Price was $1,381, price is now $624 per person
$624
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Book a stay at this luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Price was $676, price is now $341 per person
$341
per person
Feb 18 - Feb 22
found 19 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.
Level Chicago Fulton Market
Save 100% on your flight
Price was $355, price is now $184 per person
$184
per person
Feb 20 - Feb 22
found 18 hours 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.
The Emily Hotel
Save 100% on your flight
Price was $1,397, price is now $740 per person
$740
per person
Dec 30 - Jan 4
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly 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 United Center and Chicago Riverwalk are located nearby.
The Blackstone, Autograph Collection
Save 100% on your flight
Price was $326, price is now $175 per person
$175
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Trump International Hotel & Tower Chicago
Price was $784, price is now $431 per person
$431
per person
Feb 2 - Feb 5
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.
Sentral Michigan Avenue
Save 100% on your flight
Price was $904, price is now $515 per person
$515
per person
Feb 17 - Feb 22
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Soldier Field and Millennium 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, Dec 16 - Tue, Dec 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$53 Roundtrip, just found
$53
Roundtrip
just found
Tue, Dec 9 - Tue, Dec 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
Sun, Jan 25 - Thu, Jan 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Sat, Jan 17 - Thu, Jan 22
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
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