Cheap Vacations in Illinois

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Illinois vacations

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Portage I-94

OYO Hotel Portage I-94

2 out of 5
Price was $249, price is now $179 per person
$179
per person
Jan 16 - Jan 19
just found
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $470, price is now $321 per person
$321
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
Save 100% on your flight
Price was $558, price is now $387 per person
$387
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,177, price is now $818 per person
$818
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Comfort Suites Lake Geneva East

Comfort Suites Lake Geneva East

2.5 out of 5
Save 100% on your flight
Price was $321, price is now $226 per person
$226
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $529, price is now $373 per person
$373
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $704, price is now $506 per person
$506
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $382, price is now $275 per person
$275
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Lincoln

Hotel Lincoln

4 out of 5
Lincoln Park
Save 100% on your flight
Price was $262, price is now $192 per person
$192
per person
Feb 5 - Feb 8
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
The Boulevard Inn & Bistro

The Boulevard Inn & Bistro

3.5 out of 5
Save 100% on your flight
Price was $493, price is now $368 per person
$368
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)

3-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Dorothy's

Dorothy's

3 out of 5
Save 100% on your flight
Price was $224, price is now $164 per person
$164
per person
Feb 5 - Feb 8
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $490, price is now $350 per person
$350
per person
Feb 5 - Feb 8
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to Chicago (MDW)
OYO Hotel Portage I-94

OYO Hotel Portage I-94

2 out of 5
Price was $249, price is now $179 per person
$179
per person
Jan 16 - Jan 19
just found
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Price was $237, price is now $172 per person
$172
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Hotel Lincoln

Hotel Lincoln

4 out of 5
Save 100% on your flight
Price was $262, price is now $192 per person
$192
per person
Feb 5 - Feb 8
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $502, price is now $375 per person
$375
per person
Feb 5 - Feb 8
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $537, price is now $403 per person
$403
per person
Jan 18 - Jan 21
just found
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Price was $449, price is now $344 per person
$344
per person
Jan 18 - Jan 21
just found
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
Price was $1,422, price is now $1,093 per person
$1,093
per person
Feb 5 - Feb 8
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Save 100% on your flight
Price was $423, price is now $326 per person
$326
per person
Feb 5 - Feb 8
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Price was $451, price is now $349 per person
$349
per person
Jan 18 - Jan 21
just found
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Price was $486, price is now $380 per person
$380
per person
Jan 18 - Jan 21
just found
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)

4-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Comfort Suites Lake Geneva East

Comfort Suites Lake Geneva East

2.5 out of 5
Save 100% on your flight
Price was $321, price is now $226 per person
$226
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $470, price is now $321 per person
$321
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Save 100% on your flight
Price was $557, price is now $382 per person
$382
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 $593, price is now $408 per person
$408
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $482, price is now $333 per person
$333
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
Save 100% on your flight
Price was $558, price is now $387 per person
$387
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,177, price is now $818 per person
$818
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $529, price is now $373 per person
$373
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $561, price is now $399 per person
$399
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (MDW)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $382, price is now $275 per person
$275
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Price was $525, price is now $386 per person
$386
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Boulevard Inn & Bistro

The Boulevard Inn & Bistro

3.5 out of 5
Save 100% on your flight
Price was $493, price is now $368 per person
$368
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)

5-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $441, price is now $285 per person
$285
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,117, price is now $638 per person
$638
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
Price was $554, price is now $325 per person
$325
per person
Jan 29 - Feb 3
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $701, price is now $422 per person
$422
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $773, price is now $474 per person
$474
per person
Jan 23 - Jan 28
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
Price was $674, price is now $423 per person
$423
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $1,711, price is now $1,079 per person
$1,079
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Save 100% on your flight
Price was $608, price is now $387 per person
$387
per person
Jan 23 - Jan 28
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
Price was $677, price is now $433 per person
$433
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $666, price is now $435 per person
$435
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $686, price is now $448 per person
$448
per person
Jan 23 - Jan 28
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
Price was $1,388, price is now $918 per person
$918
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)

6-7 night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Price was $644, price is now $485 per person
$485
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $1,510, price is now $996 per person
$996
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was $857, price is now $601 per person
$601
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $2,023, price is now $1,426 per person
$1,426
per person
Feb 7 - Feb 13
found 3 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was $1,003, price is now $707 per person
$707
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Price was $707, price is now $521 per person
$521
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center

4 out of 5
Price was $840, price is now $627 per person
$627
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $816, price is now $611 per person
$611
per person
Feb 7 - Feb 13
found 3 hours ago
Roundtrip flight included
San Juan (SJU) 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 $801, price is now $603 per person
$603
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago - Oak Brook

DoubleTree by Hilton Chicago - Oak Brook

4 out of 5
Price was $746, price is now $572 per person
$572
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hyatt Place Chicago/ Schaumburg

Hyatt Place Chicago/ Schaumburg

3 out of 5
Price was $748, price is now $577 per person
$577
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Four Points by Sheraton Chicago Schaumburg

Four Points by Sheraton Chicago Schaumburg

3 out of 5
Price was $704, price is now $545 per person
$545
per person
Jan 21 - Jan 28
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.

Thu, Jan 29 - Sun, Feb 1
EWR
New York
ORD
Chicago
$72 Roundtrip, found 2 days ago
$72
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $72 found 2 days ago
Wed, Jan 21 - Fri, Jan 23
ATL
Atlanta
ORD
Chicago
$78 Roundtrip, found 4 days ago
$78
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Atlanta to Chicago, returning Fri, Jan 23, priced at $78 found 4 days ago
Thu, Jan 29 - Sun, Feb 1
JFK
New York
ORD
Chicago
$80 Roundtrip, found 2 days ago
$80
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $80 found 2 days ago
Thu, Jan 29 - Sun, Feb 1
LGA
New York
ORD
Chicago
$83 Roundtrip, found 2 days ago
$83
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $83 found 2 days ago
Fri, Jan 16 - Mon, Jan 19
ATL
Atlanta
STL
St. Louis
$88 Roundtrip, found 8 hours ago
$88
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Atlanta to St. Louis, returning Mon, Jan 19, priced at $88 found 8 hours ago
Fri, Jan 9 - Mon, Jan 12
DFW
Dallas
ORD
Chicago
$94 Roundtrip, found 3 days ago
$94
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Dallas to Chicago, returning Mon, Jan 12, priced at $94 found 3 days ago

Top rated hotels for your Illinois vacation

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
146.14 mi from city center
$81 nightly
The price is $95 total per night
$95 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at Hilton Chicago/Magnificent Mile Suites, you'll be centrally located in Chicago, steps from Michigan Avenue and 8 minutes by foot from Lake Michigan.
Pet friendly
Free WiFi
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
144.99 mi from city center
$127 nightly
The price is $149 total per night
$149 total
Dec 27 - Dec 28
Total with taxes and fees
Silversmith Hotel Chicago Downtown is in the heart of Chicago, within a 5-minute walk of Millennium Park and CIBC Theatre.
Free WiFi
Air conditioning
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
145.35 mi from city center
$88 nightly
The price is $103 total per night
$103 total
Dec 16 - Dec 17
Total with taxes and fees
With a stay at Club Quarters Hotel Wacker at Michigan, Chicago, you'll be centrally located in Chicago, steps from Chicago Riverwalk and 5 minutes by foot from Michigan Avenue.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Illinois
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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.