Cheap Vacations in Illinois

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Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
O'Hare
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Glen Club

The Glen Club

3.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)

3-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

3.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) 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
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)

4-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) 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
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

5-night Illinois vacations

Price found within the past 48 hours. Click for updated prices.
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) 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
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
per person
Jun 30 - Jul 5
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
Roundtrip flight included
Boston (BOS) 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, an IHG Hotel

Holiday Inn Express & Suites Prospect Heights, an IHG Hotel

3 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Sheraton Lisle Naperville Hotel

Sheraton Lisle Naperville Hotel

3.5 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
HYATT house Chicago/Schaumburg

HYATT house Chicago/Schaumburg

3.5 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
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
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hyatt Place Chicago/Naperville/Warrenville

Hyatt Place Chicago/Naperville/Warrenville

3 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Springhill Suites By Marriott Bolingbrook

Springhill Suites By Marriott Bolingbrook

3 out of 5
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Residence Inn by Marriott O'Hare

Residence Inn by Marriott O'Hare

3 out of 5
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Comfort Suites Oakbrook Terrace near Oakbrook Center

Comfort Suites Oakbrook Terrace near Oakbrook Center

3 out of 5
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Holiday Inn Chicago - Elk Grove, an IHG Hotel

Holiday Inn Chicago - Elk Grove, an IHG Hotel

3.5 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Holiday Inn Express & Suites Chicago O'Hare Airport, an IHG Hotel

Holiday Inn Express & Suites Chicago O'Hare Airport, an IHG Hotel

3 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
HYATT house Chicago/Naperville/Warrenville

HYATT house Chicago/Naperville/Warrenville

3 out of 5
per person
Jul 3 - Jul 10
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

Top places to visit in Illinois

Chicago which includes street scenes, a city and a skyscraper
FlightsFlightsHotelsHotels

Chicago

Chicago

Flight deals to Illinois

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

Wed, Jun 19 - Wed, Jun 26
DFW
Dallas
STL
St. Louis
$48 Roundtrip, found 2 days ago
$48
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jun 19 from Dallas to St. Louis, returning Wed, Jun 26, priced at $48 found 2 days ago
Tue, Aug 27 - Tue, Sep 10
ATL
Atlanta
MDW
Chicago
$48 Roundtrip, found 4 days ago
$48
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Aug 27 from Atlanta to Chicago, returning Tue, Sep 10, priced at $48 found 4 days ago
Tue, May 21 - Wed, May 22
LGA
New York
ORD
Chicago
$54 Roundtrip, found 4 days ago
$54
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, May 21 from New York to Chicago, returning Wed, May 22, priced at $54 found 4 days ago
Tue, May 21 - Wed, May 22
DFW
Dallas
ORD
Chicago
$66 Roundtrip, found 6 days ago
$66
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, May 21 from Dallas to Chicago, returning Wed, May 22, priced at $66 found 6 days ago
Tue, Jul 23 - Tue, Aug 6
ATL
Atlanta
ORD
Chicago
$68 Roundtrip, found 13 hours ago
$68
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Jul 23 from Atlanta to Chicago, returning Tue, Aug 6, priced at $68 found 13 hours ago
Tue, May 21 - Wed, May 29
DFW
Dallas
MDW
Chicago
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 21 from Dallas to Chicago, returning Wed, May 29, priced at $73 found 1 day 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
The price is $175 per night
$175
per night
May 15 - May 16
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
145.8 mi from city center
The price is $115 per night
$115
per night
May 27 - May 28
With a stay at Warwick Allerton - Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 11 minutes by foot from Chicago Riverwalk.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
146.06 mi from city center
The price is $146 per night
$146
per night
May 27 - May 28
A stay at The Westin Michigan Avenue Chicago places you in the heart of Chicago, steps from Michigan Avenue and John Hancock Center.
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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.