Great River Road Vacation Packages for 2026
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Great River Road Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $820, price is now $643 per person
$643
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,309, price is now $869 per person
$869
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Price to high for the quality.
Reviewed on Nov 9, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,182, price is now $842 per person
$842
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Everything really nice rooms and the view was amazing !!
Reviewed on Nov 9, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,942, price is now $1,430 per person
$1,430
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) 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.
Very good service
Reviewed on Nov 9, 2026
Swissotel - Chicago
Downtown Chicago
Price was $1,165, price is now $882 per person
$882
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Park Hyatt Chicago
Downtown Chicago
Price was $1,972, price is now $1,547 per person
$1,547
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jan 12 - Wed, Jan 13
ATL
Hartsfield-Jackson Atlanta Intl.
MSY
Louis Armstrong New Orleans Intl.
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
Wed, Nov 25 - Tue, Dec 1
ORD
O'Hare Intl.
MSP
Minneapolis - St. Paul Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Sat, Dec 19 - Mon, Dec 21
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$154 Roundtrip, found 18 hours ago
$154
Roundtrip
found 18 hours ago
Fri, Dec 25 - Thu, Dec 31
DFW
Dallas-Fort Worth Intl.
MSP
Minneapolis - St. Paul Intl.
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Mon, May 10 - Thu, May 13
JFK
John F. Kennedy Intl.
MSY
Louis Armstrong New Orleans Intl.
$285 Roundtrip, found 2 days ago
$285
Roundtrip
found 2 days ago