Cheap Vacations in Illinois

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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
Downtown Chicago
Save 100% on your flight
Price was $314, price is now $211 per person
$211
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
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 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $673, price is now $475 per person
$475
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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
Downtown Chicago
Save 100% on your flight
Price was $402, price is now $293 per person
$293
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Price was $382, price is now $279 per person
$279
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $543, price is now $401 per person
$401
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $576, price is now $429 per person
$429
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $303, price is now $226 per person
$226
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $695, price is now $520 per person
$520
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was $340, price is now $254 per person
$254
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Mesa (AZA) 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 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $467, price is now $335 per person
$335
per person
Feb 12 - Feb 15
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) 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 $382, price is now $279 per person
$279
per person
Jan 22 - Jan 25
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
Price was $504, price is now $372 per person
$372
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $1,095, price is now $827 per person
$827
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Chicago Marriott Suites Deerfield

Chicago Marriott Suites Deerfield

4 out of 5
Price was $271, price is now $206 per person
$206
per person
Feb 12 - Feb 15
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $360, price is now $282 per person
$282
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Save 100% on your flight
Price was $408, price is now $324 per person
$324
per person
Feb 12 - Feb 15
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
SpringHill Suites by Marriott Chicago Naperville/Warrenville

SpringHill Suites by Marriott Chicago Naperville/Warrenville

3 out of 5
Price was $428, price is now $341 per person
$341
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Price was $230, price is now $183 per person
$183
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Phoenix (PHX) 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 $446, price is now $361 per person
$361
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Price was $353, price is now $287 per person
$287
per person
Jan 29 - Feb 1
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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
Save 100% on your flight
Price was $314, price is now $211 per person
$211
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $433, price is now $280 per person
$280
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) 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 $525, price is now $347 per person
$347
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $466, price is now $313 per person
$313
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) 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 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,126, price is now $778 per person
$778
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $480, price is now $335 per person
$335
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
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 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $321, price is now $226 per person
$226
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) 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 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 $441, price is now $314 per person
$314
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) 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 $412, price is now $295 per person
$295
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)

5-night Illinois vacations

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

Hilton Chicago/Oak Brook Suites

3.5 out of 5
Price was $516, price is now $373 per person
$373
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,609, price is now $960 per person
$960
per person
Jan 18 - Jan 23
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,025, price is now $620 per person
$620
per person
Jan 18 - Jan 23
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) 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 $740, price is now $478 per person
$478
per person
Jan 18 - Jan 23
found 13 hours ago
Roundtrip 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 $967, price is now $627 per person
$627
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $794, price is now $519 per person
$519
per person
Jan 18 - Jan 23
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Save 100% on your flight
Price was $609, price is now $411 per person
$411
per person
Feb 5 - Feb 10
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
Price was $688, price is now $470 per person
$470
per person
Jan 18 - Jan 23
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Price was $720, price is now $497 per person
$497
per person
Jan 18 - Jan 23
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) 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
Save 100% on your flight
Price was $645, price is now $455 per person
$455
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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
Price was $615, price is now $436 per person
$436
per person
Jan 18 - Jan 23
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $641, price is now $460 per person
$460
per person
Jan 18 - Jan 23
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) 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 $572, price is now $426 per person
$426
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $1,438, price is now $945 per person
$945
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,828, price is now $1,223 per person
$1,223
per person
Feb 6 - Feb 12
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $751, price is now $518 per person
$518
per person
Feb 6 - Feb 12
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) to Chicago (ORD)
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Save 100% on your flight
Price was $778, price is now $542 per person
$542
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) 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
Save 100% on your flight
Price was $922, price is now $652 per person
$652
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) 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 $628, price is now $459 per person
$459
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) 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 $767, price is now $564 per person
$564
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) 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 $722, price is now $535 per person
$535
per person
Feb 6 - Feb 12
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) 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 $727, price is now $543 per person
$543
per person
Feb 6 - Feb 12
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) 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 $694, price is now $522 per person
$522
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $744, price is now $562 per person
$562
per person
Feb 6 - Feb 12
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) 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.

Wed, Jan 14 - Sat, Jan 17
ATL
Atlanta
ORD
Chicago
$68 Roundtrip, found 7 hours ago
$68
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Jan 14 from Atlanta to Chicago, returning Sat, Jan 17, priced at $68 found 7 hours ago
Thu, Jan 29 - Sun, Feb 1
EWR
New York
ORD
Chicago
$72 Roundtrip, found 4 days ago
$72
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $72 found 4 days ago
Fri, Jan 23 - Sun, Jan 25
JFK
New York
ORD
Chicago
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 23 from New York to Chicago, returning Sun, Jan 25, priced at $80 found 1 day ago
Wed, Feb 25 - Mon, Mar 2
LGA
New York
ORD
Chicago
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Feb 25 from New York to Chicago, returning Mon, Mar 2, priced at $82 found 1 day ago
Fri, Jan 9 - Mon, Jan 12
DFW
Dallas
ORD
Chicago
$94 Roundtrip, found 5 days ago
$94
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Dallas to Chicago, returning Mon, Jan 12, priced at $94 found 5 days ago
Fri, Jan 16 - Mon, Jan 19
ATL
Atlanta
STL
St. Louis
$105 Roundtrip, found 15 hours ago
$105
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Atlanta to St. Louis, returning Mon, Jan 19, priced at $105 found 15 hours 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 6 - Jan 7, 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.
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
Jan 4 - Jan 5, 2026
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.
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 23 - Dec 24
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.
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.