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 $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.
Location is great. Room is small.
Reviewed on Nov 8, 2026
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.
The staff were more ghan helpful even when checking in after midnight
The room was very spacious and clean
The breakfast selection catered for everyone with good quality food foe everyone
Had a wonderful stay, could not find a fault
Thank you for your hospitality during our stsy
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.
Good but the condition of the room wasn’t the best.
Reviewed on Nov 8, 2026
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $843, price is now $674 per person
$674
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 breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
Price was $1,011, price is now $811 per person
$811
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 a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
our shower handle broke. The guy came and fixed it, but he didn’t and had to have someone come back to fix it again. It was just a little inconvenient.
Reviewed on Nov 8, 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was $976, price is now $785 per person
$785
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 WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Very disorganized and while stay was a mess beyond the first night
Reviewed on Nov 9, 2026
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 2 - Wed, Dec 16
DFW
Dallas
MDW
Chicago
$108 Roundtrip, found 6 days ago
$108
Roundtrip
found 6 days ago
Tue, Dec 15 - Sat, Dec 19
ATL
Atlanta
ORD
Chicago
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Fri, Dec 11 - Mon, Dec 14
DAL
Dallas
MDW
Chicago
$289 Roundtrip, just found
$289
Roundtrip
just found
Wed, Dec 16 - Sun, Jan 3
ATL
Atlanta
BMI
Bloomington
$349 Roundtrip, found 4 days ago
$349
Roundtrip
found 4 days ago