Cheap Vacations in Illinois

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Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
Save 100% on your flight
Price was $298, price is now $230 per person
$230
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $554, price is now $353 per person
$353
per person
Apr 10 - Apr 12
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $726, price is now $477 per person
$477
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $605, price is now $419 per person
$419
per person
Apr 17 - Apr 20
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $577, price is now $408 per person
$408
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $866, price is now $616 per person
$616
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel 55

Hotel 55

4 out of 5
Downtown Chicago
Price was $665, price is now $487 per person
$487
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $557, price is now $438 per person
$438
per person
Apr 10 - Apr 12
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay One Chicago

Stay One Chicago

2 out of 5
Downtown Chicago
Price was $1,312, price is now $1,032 per person
$1,032
per person
Apr 6 - Apr 10
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was $436, price is now $344 per person
$344
per person
Apr 10 - Apr 12
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)

3-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
Price was $419, price is now $312 per person
$312
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $660, price is now $347 per person
$347
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $648, price is now $437 per person
$437
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $605, price is now $419 per person
$419
per person
Apr 17 - Apr 20
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Price was $462, price is now $327 per person
$327
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $809, price is now $574 per person
$574
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Houston (HOU) to St. Louis (STL)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $551, price is now $395 per person
$395
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $619, price is now $445 per person
$445
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $588, price is now $434 per person
$434
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Price was $714, price is now $529 per person
$529
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Price was $702, price is now $521 per person
$521
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Price was $466, price is now $349 per person
$349
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

4-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
Price was $484, price is now $349 per person
$349
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $807, price is now $405 per person
$405
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Price was $1,040, price is now $677 per person
$677
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $726, price is now $477 per person
$477
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $951, price is now $642 per person
$642
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Price was $584, price is now $397 per person
$397
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $906, price is now $631 per person
$631
per person
Apr 16 - Apr 20
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $807, price is now $575 per person
$575
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $816, price is now $585 per person
$585
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Price was $911, price is now $653 per person
$653
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Price was $620, price is now $446 per person
$446
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $766, price is now $552 per person
$552
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

5-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Price was $433, price is now $314 per person
$314
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $981, price is now $505 per person
$505
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $732, price is now $497 per person
$497
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
Price was $692, price is now $482 per person
$482
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) 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
Price was $745, price is now $524 per person
$524
per person
Apr 1 - Apr 6
found 15 hours ago
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
Price was $926, price is now $659 per person
$659
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $751, price is now $541 per person
$541
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $742, price is now $546 per person
$546
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $737, price is now $542 per person
$542
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $523, price is now $387 per person
$387
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) 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
Price was $703, price is now $525 per person
$525
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $760, price is now $568 per person
$568
per person
Apr 1 - Apr 6
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

6-7 night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Price was $618, price is now $436 per person
$436
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,155, price is now $560 per person
$560
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) 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
Price was $1,165, price is now $764 per person
$764
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
The Wade

The Wade

4.5 out of 5
Save 100% on your flight
Price was $908, price is now $601 per person
$601
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,027, price is now $725 per person
$725
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
Price was $935, price is now $675 per person
$675
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $961, price is now $695 per person
$695
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was $748, price is now $544 per person
$544
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,085, price is now $797 per person
$797
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

4 out of 5
Save 100% on your flight
Price was $881, price is now $659 per person
$659
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $999, price is now $751 per person
$751
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
Price was $863, price is now $658 per person
$658
per person
Apr 9 - Apr 15
just found
Roundtrip flight included
Omaha (OMA) 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

Flight deals to Illinois

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

Sat, Apr 18 - Mon, Apr 20
EWR
New York
ORD
Chicago
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Apr 18 from New York to Chicago, returning Mon, Apr 20, priced at $58 found 1 day ago
Tue, Mar 24 - Tue, Mar 31
EWR
New York
MDW
Chicago
$66 Roundtrip, found 2 days ago
$66
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Mar 24 from New York to Chicago, returning Tue, Mar 31, priced at $66 found 2 days ago
Fri, Apr 17 - Sun, Apr 19
DFW
Dallas
ORD
Chicago
$71 Roundtrip, found 1 day ago
$71
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 17 from Dallas to Chicago, returning Sun, Apr 19, priced at $71 found 1 day ago
Sat, May 30 - Tue, Jun 2
ATL
Atlanta
ORD
Chicago
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, May 30 from Atlanta to Chicago, returning Tue, Jun 2, priced at $72 found 1 day ago
Mon, Mar 16 - Tue, Mar 17
LGA
New York
ORD
Chicago
$74 Roundtrip, found 6 days ago
$74
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Mar 16 from New York to Chicago, returning Tue, Mar 17, priced at $74 found 6 days ago
Mon, Mar 23 - Thu, Mar 26
JFK
New York
ORD
Chicago
$80 Roundtrip, found 3 days ago
$80
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Mar 23 from New York to Chicago, returning Thu, Mar 26, priced at $80 found 3 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
$93 nightly
The price is $109 total per night
$109 total
Feb 23 - Feb 24
Total with taxes and fees
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
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
145.75 mi from city center
$123 nightly
The price is $144 total per night
$144 total
Mar 4 - Mar 5
Total with taxes and fees
With a stay at Hotel Riu Plaza Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 10 minutes by foot from Chicago Riverwalk.
Breakfast included
Free WiFi
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
Free Cancellation
Reserve now, pay when you stay
145.57 mi from city center
$98 nightly
The price is $116 total per night
$116 total
Mar 4 - Mar 5
Total with taxes and fees
With a stay at Embassy Suites by Hilton Chicago Downtown River North, you'll be centrally located in Chicago, steps from State Street and 4 minutes by foot from Michigan Avenue.
Pool
Breakfast included
Don't see what you're looking for?
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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.