Vacation Packages to Illinois for 2026

Illinois Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $823, price is now $628 per person
$628
per person
Dec 30 - Jan 4
found 20 hours 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.
This boutique hotel is located in a great area. Our main complaint is the hotel is old and therefore it’s not insulated from noise. We could hear every conversation, siren and party that went on in the streets. Our neighbor was a big snorer so that wasn’t pleasant. Our original room was just outside the elevator, which I did not like but the staff quickly moved us to another room, so that was great. Other than that we enjoyed our stay for the convenience. Lots of great restaurants within walking distance, stores etc.
Reviewed on Nov 5, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,379, price is now $885 per person
$885
per person
Dec 30 - Jan 4
found 20 hours 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.

Eurostars Magnificent Mile
Downtown Chicago
Price was $1,218, price is now $840 per person
$840
per person
Dec 30 - Jan 4
found 20 hours 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.
El hotel es un espectáculo, empezando por la entrada y terminando por el check-out. El personal súper atento fuimos entrada celebración de cumpleaños de mi esposo y realizaron un detalle como les pedí. En fin lo recomiendo a ojos cerrado.
Reviewed on Nov 6, 2026

Swissotel - Chicago
Downtown Chicago
Price was $1,090, price is now $807 per person
$807
per person
Dec 24 - Dec 29
found 20 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.
As of Nov 5, security deposit was not returned. And the staff does not provide any assistance.
Reviewed on Nov 6, 2026

The Blackstone, Autograph Collection
Downtown Chicago
Price was $893, price is now $690 per person
$690
per person
Dec 24 - Dec 29
found 20 hours ago
Roundtrip flight included
New York (LGA) 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 Grant Park and Millennium Park are located nearby.
Top Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
232.96 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...

The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
235.62 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...

River Hotel
75 East Wacker Drive Chicago IL
234.06 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...

The Wade
644 N Lake Shore Dr Chicago IL
235.1 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
234.94 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...

Hilton Chicago
720 S Michigan Ave Chicago IL
232.69 km from city center
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
232.97 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...

The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
234.03 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...

Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
234.12 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...

L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
233.94 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...

The Godfrey Hotel Chicago
127 West Huron, at LaSalle Chicago IL
234.42 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...

Eurostars Magnificent Mile
660 North State Street Chicago IL
234.54 km from city center
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 ...

Hotel Saint Clair- Magnificent Mile
162 East Ontario Street Chicago IL
234.71 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
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.

Wed, Dec 9 - Wed, Dec 23
ATL
Atlanta
STL
St. Louis
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago

Wed, Dec 9 - Wed, Dec 23
ATL
Atlanta
STL
St. Louis
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago

Wed, Dec 9 - Wed, Dec 23
ATL
Atlanta
STL
St. Louis
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago

Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles
ORD
Chicago
$237 Roundtrip, found 6 days ago
$237
Roundtrip
found 6 days ago

