Cheap Vacations in Illinois

Choose two or more items and save on your trip:

Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $211, price is now $145 per person
$145
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $427, price is now $282 per person
$282
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $254, price is now $169 per person
$169
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $780, price is now $521 per person
$521
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was $221, price is now $153 per person
$153
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Holiday Inn Chicago SW-Countryside ConfCtr by IHG

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

3.5 out of 5
Price was $562, price is now $387 per person
$387
per person
Jan 26 - Feb 2
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $218, price is now $151 per person
$151
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $318, price is now $226 per person
$226
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
OYO Hotel Portage I-94

OYO Hotel Portage I-94

2 out of 5
Price was $289, price is now $207 per person
$207
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was $638, price is now $457 per person
$457
per person
Jan 26 - Feb 2
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)

3-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Save 100% on your flight
Price was $291, price is now $215 per person
$215
per person
Jan 25 - Jan 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $780, price is now $521 per person
$521
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $371, price is now $261 per person
$261
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $491, price is now $356 per person
$356
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $305, price is now $225 per person
$225
per person
Jan 22 - Jan 25
found 22 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $523, price is now $388 per person
$388
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
New Orleans (MSY) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $513, price is now $383 per person
$383
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
Price was $320, price is now $239 per person
$239
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $431, price is now $324 per person
$324
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was $375, price is now $286 per person
$286
per person
Jan 21 - Jan 24
found 17 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Price was $309, price is now $241 per person
$241
per person
Jan 25 - Jan 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Price was $321, price is now $251 per person
$251
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $289, price is now $207 per person
$207
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,029, price is now $677 per person
$677
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
New Orleans (MSY) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $427, price is now $282 per person
$282
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $471, price is now $315 per person
$315
per person
Jan 28 - Feb 1
found 9 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $405, price is now $275 per person
$275
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $518, price is now $356 per person
$356
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $362 per person
$362
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $318, price is now $226 per person
$226
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $479, price is now $340 per person
$340
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $440, price is now $317 per person
$317
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
New Orleans (MSY) 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 $489, price is now $354 per person
$354
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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 $458, price is now $333 per person
$333
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)

5-night Illinois vacations

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

Kinzie Hotel

4 out of 5
Price was $583, price is now $411 per person
$411
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop 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 $982, price is now $572 per person
$572
per person
Jan 13 - Jan 18
found 20 hours 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
Save 100% on your flight
Price was $1,077, price is now $633 per person
$633
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop 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 $717, price is now $436 per person
$436
per person
Jan 13 - Jan 18
found 20 hours 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 $808, price is now $500 per person
$500
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $689, price is now $454 per person
$454
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Price was $691, price is now $484 per person
$484
per person
Jan 13 - Jan 18
found 20 hours 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
Price was $721, price is now $512 per person
$512
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Price was $640, price is now $455 per person
$455
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Price was $650, price is now $464 per person
$464
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Price was $583, price is now $422 per person
$422
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Price was $735, price is now $542 per person
$542
per person
Jan 13 - Jan 18
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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
Price was $480, price is now $295 per person
$295
per person
Jan 13 - Jan 19
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
Price was $1,371, price is now $726 per person
$726
per person
Jan 26 - Feb 2
found 24 hours ago
Roundtrip non-stop 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 $708, price is now $383 per person
$383
per person
Jan 13 - Jan 19
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 $805, price is now $448 per person
$448
per person
Jan 13 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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 $809, price is now $452 per person
$452
per person
Jan 13 - Jan 19
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
Save 100% on your flight
Price was $673, price is now $408 per person
$408
per person
Jan 26 - Feb 2
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $936, price is now $568 per person
$568
per person
Jan 26 - Feb 2
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 $703, price is now $439 per person
$439
per person
Jan 13 - Jan 19
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 $877, price is now $549 per person
$549
per person
Jan 26 - Feb 2
found 24 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 $1,398, price is now $888 per person
$888
per person
Jan 26 - Feb 2
found 24 hours 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 $630, price is now $409 per person
$409
per person
Jan 13 - Jan 19
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 $1,878, price is now $1,218 per person
$1,218
per person
Jan 26 - Feb 2
found 24 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 14 hours ago
$72
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $72 found 14 hours ago
Thu, Jan 29 - Sat, Jan 31
ATL
Atlanta
MDW
Chicago
$74 Roundtrip, found 5 days ago
$74
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jan 29 from Atlanta to Chicago, returning Sat, Jan 31, priced at $74 found 5 days ago
Thu, Jan 29 - Sat, Jan 31
ATL
Atlanta
ORD
Chicago
$74 Roundtrip, found 5 days ago
$74
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jan 29 from Atlanta to Chicago, returning Sat, Jan 31, priced at $74 found 5 days ago
Thu, Jan 29 - Sun, Feb 1
JFK
New York
ORD
Chicago
$80 Roundtrip, found 14 hours ago
$80
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $80 found 14 hours ago
Thu, Jan 29 - Sun, Feb 1
LGA
New York
ORD
Chicago
$83 Roundtrip, found 8 hours ago
$83
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $83 found 8 hours ago
Mon, Jan 19 - Fri, Jan 23
ATL
Atlanta
STL
St. Louis
$89 Roundtrip, found 3 days ago
$89
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jan 19 from Atlanta to St. Louis, returning Fri, Jan 23, priced at $89 found 3 days ago

Top rated hotels for your Illinois vacation

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
$96 nightly
The price is $113 total per night
$113 total
Jan 6 - Jan 7, 2026
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
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 21 - Dec 22
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
Don't see what you're looking for?
See all available properties in Illinois
View all properties
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.