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Illinois vacations

Prices and availability subject to change. Additional terms may apply.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
per person
May 31 - Jun 2
Roundtrip flight included
Charlotte (CLT) to St. Louis (STL)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2.5 out of 5
O'Hare
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Arista

Hotel Arista

4.5 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)

3-night Illinois vacations

Prices and availability subject to change. Additional terms may apply.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip non-stop 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 non-stop flight included
Charlotte (CLT) 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 6 - Jun 9
Roundtrip non-stop flight included
Charlotte (CLT) 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 12 - Jun 15
Roundtrip flight included
Los Angeles (LAX) 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 6 - Jun 9
Roundtrip non-stop flight included
Charlotte (CLT) 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 non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

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

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip non-stop flight included
Charlotte (CLT) 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 6 - Jun 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip non-stop 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 non-stop flight included
Charlotte (CLT) to Chicago (ORD)

4-night Illinois vacations

Prices and availability subject to change. Additional terms may apply.
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
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) 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 5 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) 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
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 9
Roundtrip flight included
Los Angeles (LAX) 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 5 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
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
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) 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 9
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

5-night Illinois vacations

Prices and availability subject to change. Additional terms may apply.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) 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 11
Roundtrip non-stop flight included
Orlando (MCO) 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 1 - Jun 6
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 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) 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 6 - Jun 11
Roundtrip non-stop 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 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) 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 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) 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 1 - Jun 6
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 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)

6-7 night Illinois vacations

Prices and availability subject to change. Additional terms may apply.
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 3 - Jun 9
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
Roundtrip non-stop flight included
Los Angeles (LAX) 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 3 - Jun 9
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 3 - Jun 9
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

4.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
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 3 - Jun 9
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
Roundtrip non-stop 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 3 - Jun 9
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
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 3 - Jun 9
Roundtrip non-stop 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.

Wed, May 8 - Sat, May 11
ATL
Atlanta
ORD
Chicago
$53 Roundtrip, found 1 hour ago
$53
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, May 8 from Atlanta to Chicago, returning Sat, May 11, priced at $53 found 1 hour ago
Tue, May 14 - Tue, May 21
DFW
Dallas
MDW
Chicago
$53 Roundtrip, found 1 day ago
$53
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 14 from Dallas to Chicago, returning Tue, May 21, priced at $53 found 1 day ago
Tue, May 14 - Tue, May 14
ATL
Atlanta
MDW
Chicago
$53 Roundtrip, found 1 day ago
$53
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 14 from Atlanta to Chicago, returning Tue, May 14, priced at $53 found 1 day ago
Tue, May 14 - Wed, May 15
LGA
New York
ORD
Chicago
$61 Roundtrip, found 4 days ago
$61
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, May 14 from New York to Chicago, returning Wed, May 15, priced at $61 found 4 days ago
Wed, May 8 - Tue, May 21
DFW
Dallas
ORD
Chicago
$68 Roundtrip, found 20 hours ago
$68
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Wed, May 8 from Dallas to Chicago, returning Tue, May 21, priced at $68 found 20 hours ago
Sat, May 18 - Tue, May 21
LAX
Los Angeles
ORD
Chicago
$104 Roundtrip, found 4 days ago
$104
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, May 18 from Los Angeles to Chicago, returning Tue, May 21, priced at $104 found 4 days 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 $128 per night
$128
per night
Apr 28 - Apr 29
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 $149 per night
$149
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 $160 per night
$160
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.