Illinois Holidays & Package Deals 2026

Top destinations in Illinois

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

Our guide on where to stay in Illinois

Find the best Illinois areas for the activities you enjoy most.

A cityscape with tall skyscrapers and a historic tower.

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.

Find hotel + flight trips in Downtown Chicago

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

Magnificent Mile

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

Find hotel + flight trips in Magnificent Mile

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.

Find hotel + flight trips in The Loop

A large, historic building with a central tower and multiple windows, located near a body of water.

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.

Find hotel + flight trips in River North

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotel + flight trips in Lincoln Park

Our pick of the best Illinois Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

NZ$245

22 Nov - 23 Nov

includes taxes & fees

8/10 Very good! (10,066 reviews)

"Excellent location- within easy walking distance of the art museum, the Bean, the lake and Studebaker Theater. If you don't mind the quirks that come with an historic property, this is a wonderful option. We had an amazing lake view from our room with high ceilings"

Reviewed on 31 Oct 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

NZ$283

19 Nov - 20 Nov

includes taxes & fees

8/10 Very good! (2,624 reviews)

"I was charged $24.00 for a glass of Gin and tonic...carpet in my room was flooded with water...mattress was horrible ... will never return.."

Reviewed on 30 Oct 2026

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

NZ$251

23 Nov - 24 Nov

includes taxes & fees

See all 10,662 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 homes 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.