Rent a ride

Illinois vacations

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) 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 6 - Jun 10
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2.5 out of 5
O'Hare
Save 100% on your flight
per person
May 29 - Jun 2
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

2.5 out of 5
Save 100% on your flight
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (CHI)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 23 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Ramada by Wyndham Glendale Heights/Lombard

Ramada by Wyndham Glendale Heights/Lombard

2.5 out of 5
Save 100% on your flight
per person
May 22 - May 26
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Gurnee Motel

Gurnee Motel

2 out of 5
per person
May 22 - May 26
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District

3 out of 5
Near West Side
Save 100% on your flight
per person
May 23 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 1 - Jun 5
Roundtrip non-stop flight included
Ontario (ONT) to Chicago (ORD)
The Glen Club

The Glen Club

3.5 out of 5
per person
Jun 1 - Jun 5
Roundtrip non-stop flight included
Ontario (ONT) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

3-night Illinois vacations

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
May 24 - May 27
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

2.5 out of 5
Save 100% on your flight
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (CHI)
Ramada by Wyndham Glendale Heights/Lombard

Ramada by Wyndham Glendale Heights/Lombard

2.5 out of 5
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Save 100% on your flight
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Hilton Garden Inn Chicago OHare Airport

Hilton Garden Inn Chicago OHare Airport

3 out of 5
Save 100% on your flight
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Renaissance Chicago North Shore Hotel

Renaissance Chicago North Shore Hotel

4 out of 5
Save 100% on your flight
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Baymont by Wyndham Glenview

Baymont by Wyndham Glenview

3 out of 5
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Super 8 by Wyndham Mundelein/Libertyville Area

Super 8 by Wyndham Mundelein/Libertyville Area

2 out of 5
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

4-night Illinois vacations

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) 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 6 - Jun 10
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2.5 out of 5
Save 100% on your flight
per person
May 29 - Jun 2
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Ramada by Wyndham Glendale Heights/Lombard

Ramada by Wyndham Glendale Heights/Lombard

2.5 out of 5
Save 100% on your flight
per person
May 22 - May 26
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hotel Arista

Hotel Arista

4.5 out of 5
Save 100% on your flight
per person
May 29 - Jun 2
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Gurnee Motel

Gurnee Motel

2 out of 5
per person
May 22 - May 26
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District

3 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 5
Roundtrip non-stop flight included
Ontario (ONT) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 10
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
Save 100% on your flight
per person
May 29 - Jun 2
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Glen Club

The Glen Club

3.5 out of 5
per person
Jun 1 - Jun 5
Roundtrip non-stop flight included
Ontario (ONT) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

5-night Illinois vacations

Hotel Arista

Hotel Arista

4.5 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

3.5 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

3 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Baymont by Wyndham Gurnee

Baymont by Wyndham Gurnee

2.5 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Baymont by Wyndham Glenview

Baymont by Wyndham Glenview

3 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Howard Johnson by Wyndham Waukegan Great Lakes

Howard Johnson by Wyndham Waukegan Great Lakes

2 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hilton Chicago/Oak Brook Suites

Hilton Chicago/Oak Brook Suites

3.5 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Super 8 by Wyndham Bridgeview/Chicago Area

Super 8 by Wyndham Bridgeview/Chicago Area

2 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hilton Garden Inn Lake Forest Mettawa

Hilton Garden Inn Lake Forest Mettawa

3 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Best Western At O'Hare

Best Western At O'Hare

2.5 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

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.

Tue, Apr 23 - Wed, Apr 24
ATL
Atlanta
MDW
Chicago
$48 Roundtrip, found 3 days ago
$48
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Apr 23 from Atlanta to Chicago, returning Wed, Apr 24, priced at $48 found 3 days ago
Tue, May 7 - Sat, May 11
ATL
Atlanta
ORD
Chicago
$51 Roundtrip, just found
$51
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, May 7 from Atlanta to Chicago, returning Sat, May 11, priced at $51 just found
Wed, Apr 24 - Tue, Apr 30
DFW
Dallas
ORD
Chicago
$56 Roundtrip, found 3 days ago
$56
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Apr 24 from Dallas to Chicago, returning Tue, Apr 30, priced at $56 found 3 days ago
Wed, May 1 - Wed, May 8
LGA
New York
ORD
Chicago
$57 Roundtrip, found 1 day ago
$57
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, May 1 from New York to Chicago, returning Wed, May 8, priced at $57 found 1 day ago
Wed, May 1 - Tue, May 7
DFW
Dallas
MDW
Chicago
$58 Roundtrip, found 2 days ago
$58
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 1 from Dallas to Chicago, returning Tue, May 7, priced at $58 found 2 days ago
Wed, Jun 19 - Wed, Jul 10
DFW
Dallas
STL
St. Louis
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jun 19 from Dallas to St. Louis, returning Wed, Jul 10, priced at $68 found 2 days 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 $127 per night
$127
per night
Apr 28 - Apr 29
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Breakfast available
Parking available
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
145.35 mi from city center
The price is $129 per night
$129
per night
Apr 21 - Apr 22
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
Pet friendly
Parking available
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
145.65 mi from city center
The price is $150 per night
$150
per night
Apr 23 - Apr 24
With a stay at Eurostars Magnificent Mile, you'll be centrally located in Chicago, just a 4-minute walk from Michigan Avenue and 11 minutes by foot from Chicago Riverwalk.
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.