Cheap Vacations in Illinois

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Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
Chatham
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

3-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) 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
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Save 100% on your flight
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Save 100% on your flight
per person
Apr 24 - Apr 27
found 24 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

4-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
per person
Apr 10 - Apr 14
found 14 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Apr 23 - Apr 27
found 3 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

5-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Apr 18 - Apr 23
found 20 hours ago
Roundtrip flight included
San Juan (SJU) 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
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Save 100% on your flight
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
per person
Apr 18 - Apr 23
found 20 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
per person
Apr 18 - Apr 23
found 20 hours ago
Roundtrip flight included
San Juan (SJU) 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
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)

6-7 night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Save 100% on your flight
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)

Top places to visit in Illinois

Chicago which includes a city and a high rise building as well as a family
FlightsFlightsHotelsHotels

Chicago

Chicago
Rockford featuring a city and general coastal views
FlightsFlightsHotelsHotels

Rockford

Rockford
Peoria featuring a lake or waterhole, skyline and a city
FlightsFlightsHotelsHotels

Peoria

Peoria

Flight deals to Illinois

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

Wed, Apr 30 - Wed, May 7
EWR
New York
ORD
Chicago
$67 Roundtrip, found 6 days ago
$67
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Apr 30 from New York to Chicago, returning Wed, May 7, priced at $67 found 6 days ago
Tue, Apr 1 - Sat, Apr 5
ATL
Atlanta
ORD
Chicago
$73 Roundtrip, found 15 hours ago
$73
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Tue, Apr 1 from Atlanta to Chicago, returning Sat, Apr 5, priced at $73 found 15 hours ago
Wed, Mar 26 - Sun, Mar 30
DFW
Dallas
ORD
Chicago
$78 Roundtrip, found 5 hours ago
$78
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Wed, Mar 26 from Dallas to Chicago, returning Sun, Mar 30, priced at $78 found 5 hours ago
Wed, Apr 23 - Tue, Apr 29
ATL
Atlanta
MDW
Chicago
$88 Roundtrip, found 15 hours ago
$88
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Wed, Apr 23 from Atlanta to Chicago, returning Tue, Apr 29, priced at $88 found 15 hours ago
Fri, Apr 11 - Sat, Apr 12
DFW
Dallas
MDW
Chicago
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 11 from Dallas to Chicago, returning Sat, Apr 12, priced at $98 found 1 day ago
Wed, Mar 12 - Thu, Mar 13
LGA
New York
ORD
Chicago
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Mar 12 from New York to Chicago, returning Thu, Mar 13, priced at $100 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 $179 per night
$179
includes taxes & fees
$152 per night
Mar 4 - Mar 5
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Free WiFi
Restaurant
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 $113 per night
$113
includes taxes & fees
$96 per night
Mar 9 - Mar 10
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
Free WiFi
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
145.27 mi from city center
The price is $193 per night
$193
includes taxes & fees
$164 per night
Mar 6 - Mar 7
With a stay at L7 Chicago by LOTTE, you'll be centrally located in Chicago, steps from Chicago Riverwalk and Chicago Theatre.
Pet friendly
Free WiFi
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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.