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Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 13 - Jun 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Chicago Marriott Midway

Chicago Marriott Midway

3.5 out of 5
Bedford Park
Save 100% on your flight
per person
Jun 13 - Jun 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Chicago/Midway Airport

Hilton Garden Inn Chicago/Midway Airport

3 out of 5
Bedford Park
Save 100% on your flight
per person
Jun 13 - Jun 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 21
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 4 - Jun 7
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

2 out of 5
Near West Side
Save 100% on your flight
per person
May 31 - Jun 3
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Best Western Plus Chicagoland - Countryside

Best Western Plus Chicagoland - Countryside

3.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 21
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

3-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

4-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2.5 out of 5
per person
Jun 2 - Jun 6
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)

5-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Isle Casino Hotel - Bettendorf

Isle Casino Hotel - Bettendorf

3 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
OYO Hotel Moline Downtown IL I-74 North

OYO Hotel Moline Downtown IL I-74 North

2 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
Casa Loma Inn & Suites by OYO Davenport IA near I-80

Casa Loma Inn & Suites by OYO Davenport IA near I-80

2.5 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
Comfort Inn & Suites East Moline near I-80

Comfort Inn & Suites East Moline near I-80

2.5 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
Ramada by Wyndham Bettendorf

Ramada by Wyndham Bettendorf

2.5 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
Moline Bell Hotel

Moline Bell Hotel

2 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
Country Inn & Suites by Radisson, Davenport, IA

Country Inn & Suites by Radisson, Davenport, IA

2.5 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
Stoney Creek Hotel Quad Cities - Moline

Stoney Creek Hotel Quad Cities - Moline

2.5 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
DoubleTree by Hilton Davenport

DoubleTree by Hilton Davenport

4 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
Quality Inn & Suites Eldridge Davenport North

Quality Inn & Suites Eldridge Davenport North

2.5 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
Super 8 by Wyndham Davenport

Super 8 by Wyndham Davenport

2 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)
My Place Hotel - Davenport/Quad Cities IA

My Place Hotel - Davenport/Quad Cities IA

3 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Los Angeles (LAX) to Moline (MLI)

6-7 night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 21
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2.5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Top places to visit in Illinois

Chicago which includes street scenes, a city and a skyscraper
FlightsFlightsHotelsHotels

Chicago

Chicago

Flight deals to Illinois

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, May 7 - Tue, May 14
DFW
Dallas
MDW
Chicago
$48 Roundtrip, found 18 hours ago
$48
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, May 7 from Dallas to Chicago, returning Tue, May 14, priced at $48 found 18 hours ago
Tue, May 14 - Tue, May 21
ATL
Atlanta
ORD
Chicago
$48 Roundtrip, found 22 hours ago
$48
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Tue, May 14 from Atlanta to Chicago, returning Tue, May 21, priced at $48 found 22 hours ago
Tue, May 14 - Tue, May 14
ATL
Atlanta
MDW
Chicago
$53 Roundtrip, found 3 days ago
$53
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 14 from Atlanta to Chicago, returning Tue, May 14, priced at $53 found 3 days ago
Thu, May 30 - Wed, Jun 5
DFW
Dallas
ORD
Chicago
$57 Roundtrip, found 23 hours ago
$57
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Thu, May 30 from Dallas to Chicago, returning Wed, Jun 5, priced at $57 found 23 hours ago
Tue, May 14 - Wed, May 15
LGA
New York
ORD
Chicago
$61 Roundtrip, found 6 days ago
$61
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, May 14 from New York to Chicago, returning Wed, May 15, priced at $61 found 6 days ago
Sat, May 18 - Tue, May 21
LAX
Los Angeles
ORD
Chicago
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, May 18 from Los Angeles to Chicago, returning Tue, May 21, priced at $100 found 1 day ago

Top rated hotels for your Illinois vacation

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
144.67 mi from city center
The price is $127 per night
$127
per night
Apr 29 - Apr 30
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Breakfast available
Parking available
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
145.35 mi from city center
The price is $139 per night
$139
per night
Apr 28 - Apr 29
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
Pet friendly
Parking available
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
145.65 mi from city center
The price is $170 per night
$170
per night
Apr 28 - Apr 29
With a stay at Eurostars Magnificent Mile, you'll be centrally located in Chicago, just a 4-minute walk from Michigan Avenue and 11 minutes by foot from Chicago Riverwalk.
Spa
Parking available
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.