Vacation Packages to Illinois for 2026
Illinois Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$653
per person
Nov 3 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
The hotel was a good stay, and it was in a good location, but they didn't give us a room with a view. Our room was in the corner and our one window was facing a brick. Besides that, the stay was good, and the staff was friendly.
Reviewed on Sep 9, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$897
per person
Nov 3 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
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 Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,470
per person
Nov 3 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
Level Chicago Fulton Market
Downtown Chicago
$1,111
per person
Nov 3 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The pool & jacuzzi was perfect, this hotel is beautiful
Reviewed on Sep 7, 2026
The Talbott, Autograph Collection
Downtown Chicago
$967
per person
Nov 3 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Old,
Reviewed on Sep 8, 2026
Level Chicago – Old Town
Downtown Chicago
$958
per person
Nov 3 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Location and facility was very nice
Reviewed on Sep 7, 2026
Top Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
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 ...
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
River Hotel
75 East Wacker Drive Chicago IL
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 ...
Hilton Chicago
720 S Michigan Ave Chicago IL
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 ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
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 Wade
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
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 ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place Chicago IL
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 ...
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
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, Nov 4 - Mon, Nov 9
ATL
Atlanta
ORD
Chicago
$74
Roundtrip
found 10 hours ago
Wed, Oct 14 - Mon, Oct 19
ATL
Atlanta
STL
St. Louis
$76
Roundtrip
found 1 day ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles
ORD
Chicago
$217
Roundtrip
found 2 days ago
Sat, Nov 14 - Mon, Nov 16
LAX
Los Angeles
MDW
Chicago
$237
Roundtrip
found 1 day ago
Popular vacation package destinations in Illinois
- Chicago Vacations
- Galena Vacations
- Springfield Vacations
- Champaign Vacations
- Naperville Vacations
- Rockford Vacations
- Joliet Vacations
- Peoria Vacations
- Tinley Park Vacations
- Bloomington Vacations
- Aurora Vacations
- Ottawa Vacations
- Waukegan Vacations
- Bolingbrook Vacations
- Orland Park Vacations
- Elgin Vacations
- Effingham Vacations
- Carbondale Vacations
- Moline Vacations
- St. Charles Vacations
- Marion Vacations
- Utica Vacations
- Normal Vacations
- East Peoria Vacations
- O'Fallon Vacations
- Edwardsville Vacations
- Lansing Vacations
- Romeoville Vacations
- Urbana Vacations
- Mount Vernon Vacations
- Quincy Vacations
- Decatur Vacations
- Zion Vacations
- Matteson Vacations
- Collinsville Vacations
- Alton Vacations
- Geneva Vacations
- Crystal Lake Vacations
- Grafton Vacations
- Fairview Heights Vacations
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