Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
Save 100% on your flight
Price was $471, price is now $295 per person
$295
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Park Hyatt Chicago
Price was $2,197, price is now $1,221 per person
$1,221
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,200, price is now $669 per person
$669
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Level Chicago - River North
Save 100% on your flight
Price was $1,090, price is now $613 per person
$613
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. 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 $1,075, price is now $610 per person
$610
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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 $679, price is now $426 per person
$426
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
DoubleTree by Hilton Chicago - Alsip
Save 100% on your flight
Price was $553, price is now $349 per person
$349
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
Stay at this 4-star business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
La Banque Hotel
Save 100% on your flight
Price was $600, price is now $378 per person
$378
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) 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.
Wed, Dec 3 - Thu, Dec 4
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 7 hours ago
$90
Roundtrip
found 7 hours ago
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 7 hours ago
$96
Roundtrip
found 7 hours ago
Sat, Dec 6 - Tue, Dec 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$108 Roundtrip, found 8 hours ago
$108
Roundtrip
found 8 hours ago
Tue, Oct 21 - Sat, Oct 25
LGA
LaGuardia
ORD
O'Hare Intl.
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
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