Search Deals onIllinois Vacation Packages
Illinois Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield
Save 100% on your flight
per person
Jun 29 - Jul 4
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
Stay at this 3-star business-friendly hotel in Chesterfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions The J - Chesterfield Gym & Fitness Center and Topgolf are located nearby.
The Wildwood Hotel
Save 100% on your flight
per person
Jun 29 - Jul 4
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
Stay at this 3.5-star business-friendly hotel in Wildwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags St. Louis and Skid Row are located nearby.
The French Country Inn Lake Geneva
Save 100% on your flight
per person
Jul 21 - Jul 25
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star hotel in Lake Geneva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Geneva Lake and Lake Geneva Cruise Line are located nearby.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Four Points by Sheraton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Fashion Outlets of Chicago are located nearby.
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Downtown Chicago
Save 100% on your flight
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
3-4 Night Vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Illinois
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
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
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 ...
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Save an average of 15% on thousands of hotels when you're signed in
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
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 ...
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 1 hour ago
$90
Roundtrip
found 1 hour ago
Thu, Jun 12 - Tue, Jun 17
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$100 Roundtrip, found 21 hours ago
$100
Roundtrip
found 21 hours ago
Sat, Jun 21 - Tue, Jun 24
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Sat, Jul 19 - Sat, Jul 26
ATL
Hartsfield-Jackson Atlanta Intl.
STL
Lambert-St. Louis Intl.
$113 Roundtrip, found 9 hours ago
$113
Roundtrip
found 9 hours ago
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