Cheap Vacations in Illinois

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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)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $487, price is now $331 per person
$331
per person
Jan 22 - Jan 26
found 1 hour 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)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was $536, price is now $390 per person
$390
per person
Jan 27 - Jan 31
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)
Comfort Inn & Suites Geneva - West Chicago

Comfort Inn & Suites Geneva - West Chicago

2.5 out of 5
Save 100% on your flight
Price was $364, price is now $272 per person
$272
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
Price was $488, price is now $366 per person
$366
per person
Feb 5 - Feb 10
found 2 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
Downtown Chicago
Price was $537, price is now $403 per person
$403
per person
Jan 18 - Jan 21
found 6 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Price was $449, price is now $344 per person
$344
per person
Jan 18 - Jan 21
found 6 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.
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
found 5 hours ago
Roundtrip flight included
Phoenix (PHX) 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 1 day ago
Roundtrip flight included
Tampa (TPA) to Chicago (MDW)
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
Price was $382, price is now $279 per person
$279
per person
Jan 22 - Jan 25
found 2 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 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
Price was $537, price is now $403 per person
$403
per person
Jan 18 - Jan 21
found 6 hours ago
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
found 6 hours ago
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 1 day 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 1 day 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
found 6 hours ago
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
found 6 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Sheraton Suites Chicago Elk Grove

Sheraton Suites Chicago Elk Grove

3.5 out of 5
Price was $299, price is now $237 per person
$237
per person
Jan 16 - Jan 19
found 23 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $659, price is now $525 per person
$525
per person
Jan 18 - Jan 21
found 6 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)

4-night 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 $314, price is now $220 per person
$220
per person
Jan 22 - Jan 26
found 1 hour 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 $487, price is now $331 per person
$331
per person
Jan 22 - Jan 26
found 1 hour 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)
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)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $673, price is now $475 per person
$475
per person
Jan 22 - Jan 26
found 1 hour 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)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Price was $633, price is now $455 per person
$455
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
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)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $662, price is now $477 per person
$477
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $536, price is now $390 per person
$390
per person
Jan 27 - Jan 31
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
Price was $548, price is now $401 per person
$401
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)

5-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
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 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $951, price is now $557 per person
$557
per person
Jan 29 - Feb 3
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $797, price is now $489 per person
$489
per person
Jan 29 - Feb 3
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was $745, price is now $458 per person
$458
per person
Jan 29 - Feb 3
found 11 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
Price was $700, price is now $431 per person
$431
per person
Jan 29 - Feb 3
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $652, price is now $408 per person
$408
per person
Jan 29 - Feb 3
found 11 hours 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
Price was $755, price is now $485 per person
$485
per person
Jan 29 - Feb 3
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Price was $655, price is now $437 per person
$437
per person
Jan 29 - Feb 3
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Price was $641, price is now $436 per person
$436
per person
Jan 29 - Feb 3
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Price was $544, price is now $370 per person
$370
per person
Jan 29 - Feb 3
found 11 hours 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
Price was $475, price is now $328 per person
$328
per person
Jan 29 - Feb 3
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

2.5 out of 5
Price was $545, price is now $379 per person
$379
per person
Jan 29 - Feb 3
found 11 hours 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 20 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 20 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 20 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 9 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 20 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 20 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 20 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 9 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 20 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 20 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 20 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 20 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
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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 3 days ago
$72
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $72 found 3 days ago
Wed, Jan 21 - Fri, Jan 23
ATL
Atlanta
ORD
Chicago
$78 Roundtrip, found 5 days ago
$78
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Atlanta to Chicago, returning Fri, Jan 23, priced at $78 found 5 days ago
Fri, Jan 23 - Sun, Jan 25
JFK
New York
ORD
Chicago
$80 Roundtrip, found 5 hours ago
$80
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Jan 23 from New York to Chicago, returning Sun, Jan 25, priced at $80 found 5 hours 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 14 hours ago
$88
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Atlanta to St. Louis, returning Mon, Jan 19, priced at $88 found 14 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.