Vacation Packages to Illinois for 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 ...
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 ...
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 ...
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 ...
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr 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 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 ...
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 ...
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 ...
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 ...
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 breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
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 ...
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 ...
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. ...
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.
Thu, Jan 22 - Thu, Jan 29
JFK
New York
ORD
Chicago
$73 Roundtrip, found 4 days ago
$73
Roundtrip
found 4 days ago
Wed, Apr 8 - Wed, Apr 15
LGA
New York
ORD
Chicago
$84 Roundtrip, found 13 hours ago
$84
Roundtrip
found 13 hours ago
Mon, Feb 2 - Wed, Feb 4
LGA
New York
MDW
Chicago
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Mon, Jul 13 - Tue, Jul 14
DAL
Dallas
MDW
Chicago
$272 Roundtrip, found 2 days ago
$272
Roundtrip
found 2 days ago
Fri, Jan 30 - Sun, Feb 1
JFK
New York
CMI
Champaign
$338 Roundtrip, found 5 days ago
$338
Roundtrip
found 5 days ago