Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Naperville/Warrenville
Save 100% on your flight
Price was $594, price is now $403 per person
$403
per person
Sep 23 - Sep 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Warrenville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Chicago Premium Outlets and Odyssey Fun World are located nearby.
Beautiful facilities.
We knew breakfast was not included, but were shocked at the $16 price if we were interested in eating the hotel breakfast. No thanks! We headed across town the The Tasty Biscuit and had an absolutely amazing breakfast for the same price.
Reviewed on Jul 15, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,571, price is now $836 per person
$836
per person
Sep 23 - Sep 28
found 2 days 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.
Location and Customer Service of all employees, breakfast were great and varied, very good food,
Reviewed on Jul 16, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,746, price is now $1,021 per person
$1,021
per person
Sep 23 - Sep 28
found 2 days 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.
Hilton Chicago O'Hare Airport
Save 100% on your flight
Price was $1,002, price is now $638 per person
$638
per person
Sep 23 - Sep 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fashion Outlets of Chicago and Rosemont Theatre are located nearby.
Mediocre room, less mediocre food.
Reviewed on Jul 15, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,231, price is now $793 per person
$793
per person
Aug 27 - Aug 31
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 a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $2,194, price is now $1,414 per person
$1,414
per person
Sep 23 - Sep 28
found 2 days 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.
Holiday Inn Express & Suites Prospect Heights by IHG
Save 100% on your flight
Price was $602, price is now $408 per person
$408
per person
Sep 23 - Sep 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Prospect Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rob Roy Golf Course and Grove National Historic Landmark are located nearby.
Wind Creek Southland Casino and Hotel
Save 100% on your flight
Price was $809, price is now $553 per person
$553
per person
Sep 23 - Sep 28
found 2 days 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 15 - Sat, Sep 19
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 4 days ago
$102
Roundtrip
found 4 days ago
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$106 Roundtrip, found 5 hours ago
$106
Roundtrip
found 5 hours ago
Tue, Oct 27 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$149 Roundtrip, found 2 hours ago
$149
Roundtrip
found 2 hours ago
Wed, Aug 5 - Fri, Aug 14
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
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