Vacation Packages to Illinois for 2025
Illinois Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Saratoga Motel By Capital O Near Midway Airport Chicago IL
Ashburn
Save 100% on your flight
Price was $444, price is now $295 per person
$295
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and room service. Popular attraction SeatGeek Stadium is located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $726, price is now $401 per person
$401
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $569, price is now $380 per person
$380
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $503, price is now $338 per person
$338
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $708, price is now $496 per person
$496
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Congress Plaza Hotel
Downtown Chicago
Price was $492, price is now $350 per person
$350
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. 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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
234.41 km from city center
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
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 free WiFi, 2 restaurants, and 2 bars/lounges. 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 ...
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
234.01 km from city center
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
234.33 km from city center
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Aloft Chicago Mag Mile
243 E. Ontario, Chicago, IL
234.78 km from city center
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the bar in our reviews. Popular ...
Freehand Chicago
19 East Ohio Street, Chicago, IL
234.42 km from city center
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
235.1 km from city center
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
Hotel Riu Plaza Chicago
150 East Ontario Street, Chicago, IL
234.7 km from city center
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
234.45 km from city center
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
233.35 km from city center
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
Pendry Chicago
230 North Michigan Avenue, Chicago, IL
234 km from city center
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
233.39 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
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, Nov 27 - Wed, Dec 3
ATL
Atlanta
MDW
Chicago
$68 Roundtrip, found 5 days ago
$68
Roundtrip
found 5 days ago
Sun, Nov 23 - Tue, Dec 2
LGA
New York
ORD
Chicago
$100 Roundtrip, found 17 hours ago
$100
Roundtrip
found 17 hours ago
Thu, Dec 4 - Tue, Dec 9
ATL
Atlanta
ORD
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Thu, Dec 4 - Tue, Dec 9
ATL
Atlanta
ORD
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Tue, Apr 21 - Wed, Apr 22
EWR
New York
MDW
Chicago
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago