Vacation Packages to Illinois for 2026
Illinois Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
River Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,364, price is now $923 per person
$923
per person
Aug 4 - Aug 11
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
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 rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,984, price is now $1,279 per person
$1,279
per person
Jul 26 - Aug 1
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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 restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $3,389, price is now $2,319 per person
$2,319
per person
Jul 26 - Aug 1
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,593, price is now $1,097 per person
$1,097
per person
Jul 26 - Aug 1
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
Price was $2,737, price is now $1,935 per person
$1,935
per person
Jul 26 - Aug 1
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,657, price is now $1,188 per person
$1,188
per person
Aug 4 - Aug 11
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
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 rooms in our reviews. Popular attractions Grant Park and Millennium Park 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 ...
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 ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
231 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
233.05 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
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 ...
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 ...
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
232.84 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
233.35 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
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 ...
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
234.74 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 breakfast and the helpful ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
234.46 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
Freehand Chicago
19 East Ohio Street Chicago IL
234.4 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms 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.
Wed, Jul 29 - Wed, Aug 5
ATL
Atlanta
STL
St. Louis
$86 Roundtrip, found 10 hours ago
$86
Roundtrip
found 10 hours ago
Tue, Aug 18 - Tue, Sep 1
EWR
New York
ORD
Chicago
$187 Roundtrip, found 12 hours ago
$187
Roundtrip
found 12 hours ago
Tue, Jul 21 - Wed, Jul 22
JFK
New York
ORD
Chicago
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Tue, Aug 4 - Wed, Aug 5
LGA
New York
ORD
Chicago
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Thu, Oct 1 - Sun, Oct 4
LGA
New York
MDW
Chicago
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago