Vacation Packages to Illinois for 2026
Illinois Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
Save 100% on your flight
Price was $903, price is now $552 per person
$552
per person
Mar 11 - Mar 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
Book a stay at this business-friendly hotel in Wildwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags St. Louis and Skid Row are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,797, price is now $1,150 per person
$1,150
per person
Mar 22 - Mar 27
found 14 hours ago
Roundtrip flight included
Norfolk (ORF) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $970, price is now $647 per person
$647
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Norfolk (ORF) 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 Emily Hotel
Downtown Chicago
Price was $1,104, price is now $789 per person
$789
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,324, price is now $969 per person
$969
per person
Mar 22 - Mar 27
found 24 hours ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was $1,204, price is now $907 per person
$907
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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 ...
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
234.41 km from city center
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
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 ...
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
234.8 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
234.7 km from city center
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 ...
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
234.76 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
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 ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
235.34 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Courtyard by Marriott Chicago Magnificent Mile
165 East Ontario Street Chicago IL
234.71 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive Chicago IL
234.07 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
234.17 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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 ...
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 ...
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, Apr 29 - Sun, May 3
JFK
New York
ORD
Chicago
$66 Roundtrip, found 17 hours ago
$66
Roundtrip
found 17 hours ago
Sun, Feb 22 - Mon, Mar 9
EWR
New York
ORD
Chicago
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Thu, Apr 30 - Mon, May 4
LGA
New York
ORD
Chicago
$137 Roundtrip, found 17 hours ago
$137
Roundtrip
found 17 hours ago
Wed, Apr 29 - Sun, May 3
EWR
New York
ORD
Chicago
$137 Roundtrip, found 17 hours ago
$137
Roundtrip
found 17 hours ago
Wed, Apr 29 - Sun, May 3
LGA
New York
MDW
Chicago
$137 Roundtrip, found 17 hours ago
$137
Roundtrip
found 17 hours ago