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3-night Illinois vacations

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)
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)
Virgin Hotels Chicago

Virgin Hotels 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)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
per person
May 28 - May 31
Roundtrip 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)
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)
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)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
per person
May 28 - May 31
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

4-night Illinois vacations

DoubleTree by Hilton Chicago Midway Airport

DoubleTree by Hilton Chicago Midway Airport

4 out of 5
per person
Jun 1 - Jun 5
Roundtrip flight included
Washington (IAD) to Chicago (ORD)
Hilton Chicago/Oak Brook Suites

Hilton Chicago/Oak Brook Suites

3.5 out of 5
per person
Jun 1 - Jun 5
Roundtrip flight included
Washington (IAD) to Chicago (ORD)
Hampton Inn & Suites Chicago-Burr Ridge

Hampton Inn & Suites Chicago-Burr Ridge

2.5 out of 5
per person
Jun 1 - Jun 5
Roundtrip flight included
Washington (IAD) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
per person
Jun 6 - Jun 10
Roundtrip non-stop flight included
Baltimore (BWI) 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
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) 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)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 10
Roundtrip non-stop flight included
Baltimore (BWI) 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)
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)
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop

3 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

6-7 night Illinois vacations

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) 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 25 - Jun 1
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3.5 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Ramada by Wyndham Glendale Heights/Lombard

Ramada by Wyndham Glendale Heights/Lombard

2.5 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
River Hotel

River Hotel

4 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

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.

Sat, May 11 - Mon, May 13
ATL
Atlanta
ORD
Chicago
$51 Roundtrip, found 14 hours ago
$51
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Sat, May 11 from Atlanta to Chicago, returning Mon, May 13, priced at $51 found 14 hours ago
Tue, May 14 - Tue, May 21
DFW
Dallas
MDW
Chicago
$53 Roundtrip, found 13 hours ago
$53
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, May 14 from Dallas to Chicago, returning Tue, May 21, priced at $53 found 13 hours ago
Tue, May 14 - Tue, May 14
ATL
Atlanta
MDW
Chicago
$53 Roundtrip, found 12 hours ago
$53
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, May 14 from Atlanta to Chicago, returning Tue, May 14, priced at $53 found 12 hours ago
Wed, May 1 - Wed, May 8
LGA
New York
ORD
Chicago
$57 Roundtrip, found 5 days ago
$57
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, May 1 from New York to Chicago, returning Wed, May 8, priced at $57 found 5 days ago
Wed, May 15 - Mon, May 20
DFW
Dallas
ORD
Chicago
$66 Roundtrip, found 6 days ago
$66
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 15 from Dallas to Chicago, returning Mon, May 20, priced at $66 found 6 days ago
Sat, May 18 - Tue, May 21
LAX
Los Angeles
ORD
Chicago
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, May 18 from Los Angeles to Chicago, returning Tue, May 21, priced at $104 found 2 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 $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.
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.
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.
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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.