Vacation Packages to Illinois for 2026
Illinois Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago Dwtn - The Mart by IHG
Downtown Chicago
Save 100% on your flight
Price was $1,702, price is now $1,225 per person
$1,225
per person
Jul 22 - Jul 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, 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 $1,844, price is now $1,257 per person
$1,257
per person
Jul 22 - Jul 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
Hilton Garden Inn Chicago Downtown Riverwalk
Downtown Chicago
Save 100% on your flight
Price was $1,965, price is now $1,375 per person
$1,375
per person
Jul 22 - Jul 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
Save 100% on your flight
Price was $1,970, price is now $1,416 per person
$1,416
per person
Jul 22 - Jul 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,720, price is now $1,245 per person
$1,245
per person
Jul 22 - Jul 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kinzie Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,769, price is now $1,288 per person
$1,288
per person
Jul 22 - Jul 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue 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 1 hour ago
$86
Roundtrip
found 1 hour ago
Tue, Aug 18 - Tue, Sep 1
EWR
New York
ORD
Chicago
$187 Roundtrip, found 3 hours ago
$187
Roundtrip
found 3 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 16 hours ago
$187
Roundtrip
found 16 hours ago
Thu, Oct 1 - Sun, Oct 4
LGA
New York
MDW
Chicago
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago