Vacation Packages to Illinois for 2025
Illinois Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was $580, price is now $441 per person
$441
per person
Dec 16 - Dec 20
just found
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4.5-star 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $870, price is now $585 per person
$585
per person
Dec 10 - Dec 14
found 5 hours ago
Roundtrip non-stop flight included
Pasco (PSC) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,525, price is now $1,034 per person
$1,034
per person
Dec 16 - Dec 20
just found
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 5-star 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.
Arlo Chicago
Downtown Chicago
Price was $638, price is now $471 per person
$471
per person
Dec 16 - Dec 20
just found
Roundtrip flight included
Austin (AUS) 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
Price was $820, price is now $606 per person
$606
per person
Dec 16 - Dec 20
just found
Roundtrip flight included
Austin (AUS) 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.
Hilton Chicago O'Hare Airport
O'Hare
Price was $940, price is now $696 per person
$696
per person
Dec 10 - Dec 14
found 5 hours ago
Roundtrip non-stop flight included
Pasco (PSC) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex 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 6 days ago
$68
Roundtrip
found 6 days ago
Thu, Dec 4 - Tue, Dec 9
ATL
Atlanta
ORD
Chicago
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Thu, Jan 8 - Sun, Jan 11
LGA
New York
ORD
Chicago
$148 Roundtrip, found 7 hours ago
$148
Roundtrip
found 7 hours ago
Thu, Jan 8 - Sun, Jan 11
LGA
New York
ORD
Chicago
$148 Roundtrip, found 7 hours ago
$148
Roundtrip
found 7 hours ago
Tue, Apr 21 - Wed, Apr 22
EWR
New York
MDW
Chicago
$207 Roundtrip, found 6 days ago
$207
Roundtrip
found 6 days ago