Vacation Packages to Illinois for 2026

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Top Hotel Deals

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
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 ...
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
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 ...
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr 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 ...
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
233.47 km from city center
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 ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
232.69 km from city center
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 ...
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
234.53 km from city center
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 ...
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
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 ...
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
234.41 km from city center
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
235.1 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
234.79 km from city center
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 ...
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave Chicago IL
234.45 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 ...
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
234.28 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the ...
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive Chicago IL
234.09 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
900 E Grand Chicago IL
235.41 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 restaurant and the helpful ...
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
234.22 km from city center
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 ...
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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.

Frontier Airlines
Wed, Jan 14 - Sat, Jan 17
JFK
New York
ORD
Chicago
$68 Roundtrip, found 9 hours ago
$68
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Jan 14 from New York to Chicago, returning Sat, Jan 17, priced at $68 found 9 hours ago
Spirit Airlines
Tue, Jan 13 - Sun, Jan 18
LGA
New York
ORD
Chicago
$82 Roundtrip, found 9 hours ago
$82
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Tue, Jan 13 from New York to Chicago, returning Sun, Jan 18, priced at $82 found 9 hours ago
JetBlue Airways
Tue, May 19 - Wed, May 27
JFK
New York
ORD
Chicago
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, May 19 from New York to Chicago, returning Wed, May 27, priced at $170 found 1 day ago
American Airlines
Sat, Jul 4 - Thu, Jul 9
EWR
New York
ORD
Chicago
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jul 4 from New York to Chicago, returning Thu, Jul 9, priced at $187 found 4 days ago
United
Wed, Apr 29 - Sun, May 3
EWR
New York
ORD
Chicago
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select United flight, departing Wed, Apr 29 from New York to Chicago, returning Sun, May 3, priced at $187 found 1 day ago