Illinois Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Illinois

A city skyline with modern skyscrapers and a river with boats and people in the foreground.
FlightsFlightsHotelsHotels

Chicago

Chicago

Where to stay in Illinois

Find the best Illinois areas for the activities you enjoy most.
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

The Chicago Theatre with illuminated marquee and a wet street reflecting lights.
Photo by Mattyboy876
Open Photo by Mattyboy876

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top hotels in Illinois

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$211 per night from 30 Aug to 31 Aug
S$211
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (10,181 reviews)
"Check in was terrible. Took over an hour. Waited in line for 20 minutes and rooms were not ready. It was after check in time. Told to come back in twenty minutes. Immediately went to the end of the check in line and waited 40 minutes. First agent was terrible; second agent was pleasant and very helpful ..."

Reviewed on 2 Aug, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$245 per night from 16 Aug to 17 Aug
S$245
16 Aug - 17 Aug
includes taxes & fees
8/10 Very good! (1,889 reviews)
"Not a clean room, when we checked in, and unrolled the bed, the entire mattress topper had black hair, dust, and just looked soiled. We immediately called staff, and the housekeeping only brought up a change of linens and just asked us to put everything dirty in a bag and change it. Not ideal for ..."

Reviewed on 1 Aug, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 30 Aug to 31 Aug
S$247
30 Aug - 31 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
See all 10,362 properties in Illinois
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.

Frequently asked questions

How much does an Illinois holiday package cost?
We make it simple to travel somewhere new, with Illinois packages starting from as low as . You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to Illinois?
Booking an Illinois holiday package with Expedia is a great way to save. We have access to more than 550 air carriers and 1,000,000 hotel options all over the world. With such a fabulous range to choose from, you'll have no trouble pulling together your perfect escape.
Where should I stay in Illinois?
Chicago is a wonderful destination to visit. Here, you'll find popular sights including Wrigley Field and Six Flags Great America. Joliet also draws in many travellers eager to check out some of the best attractions in Illinois. These include Rialto Square Theatre and Silver Cross Field.
What are the top hotels in Illinois?
Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton know how to make their guests feel welcome in Chicago. If you also plan to explore Galena, have a look at The Whitehall Hotel and Hyatt Regency Chicago. Both are popular with travellers.
How far in advance should I book my Illinois holiday?
Browse Expedia to compare international airfares as early as possible. In most cases, you can purchase a seat up to 12 months before departure. If you don't see your preferred air carrier, or you've left things to the last moment, don't worry. Cheap fares to Illinois sometimes occur within weeks of departure.
What does an Expedia Illinois travel package include?
Rental cars, flights and hotels — we have them covered. With Expedia, you can create your Illinois travel package however you want. All you have to do is determine what you need. Once you've made your booking, you can add on fun things like tours and activities. The more you bundle, the greater the savings!
What should I know before booking an Illinois travel package?
Locking in all the parts of your holiday together is one of the easiest ways to save. Bundle car rentals, airfares and hotels into one package. But your options don't end at hotels. Expedia features all sorts of properties, including holiday rentals like mountain cabins and serviced residences. The list is almost endless!
Can I choose my airline with an Illinois Expedia holiday package?
Yes, definitely. Expedia has more than 550 airline partners to select from globally. With so much choice, finding the ideal carrier to fly you to Illinois won't be difficult.
If I'm not able to travel, can I cancel my Illinois holiday package?
Because we know life can throw you a few curveballs, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Stay near popular Illinois attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
See properties

What to do in Illinois

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

S$199
per adult
82% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
See all activities in Illinois

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.