Illinois Vacations & Trips from $409

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Your Illinois Vacation

Lock in a vacation package to Illinois and travel on your own terms. You'll be delighted by its views, dining and culture. A trip to Illinois wouldn't be complete without exploring some of its most renowned cities, starting with Chicago. Some of the most popular attractions here include Wrigley Field and Navy Pier. Schaumburg is another favorite with Illinois travelers. Visitors to this exciting city enjoy Woodfield Mall and Schaumburg Convention Center. From the moment you book your Illinois vacation to when you return home, Expedia has you covered each step of the way.

Top destinations in Illinois

Chicago which includes a city and a high rise building as well as a family
FlightsFlightsHotelsHotels

Chicago

Chicago

The Latest Illinois Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $798, price is now $409 per person
$409
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Wonderful staff! Convenient location for walking to restaurants, shopping and right next to a subway station

Reviewed on Aug 30, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,644, price is now $804 per person
$804
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug 22, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $1,003, price is now $495 per person
$495
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,562 reviews)
Very quiet, nice area. Walkable to restaurants and shops. The staff was extremely welcoming. This is a beautiful facility and is even pet friendly. I would highly recommend this hotel if you need to stay in this area.

Reviewed on Aug 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,196, price is now $1,173 per person
$1,173
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug 29, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $891, price is now $500 per person
$500
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
My niece and I loved it here! Staff was excellent. Very knowledgeable, efficient, friendly. Beds & pillows were comfortable. Enjoyed the scent of the bathroom toiletries. Nice view of city from our room. Convenient location with lots of good restaurants close by. Not far to get to train. Love that they allow dogs & cats. (We didn’t bring our dogs but it was nice to see a dog there). Very quiet room. Wasn’t the typical loud hallways and slamming doors situation. Would absolutely stay here again!

Reviewed on Aug 30, 2025

Where to stay in Illinois

Get a lay of the land and find the perfect place to stay Learn more about Illinois
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

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

Find hotels in Downtown Chicago

Best Places to Vacation in Illinois

1. Find your perfect Chicago vacation

Chicago is renowned as a vibrant city that offers a diverse range of experiences for families. With its iconic skyline and impressive architecture, the city is a paradise for urban enthusiasts. From exploring the renowned theater scene to visiting world-class museums, there is something for everyone. Families can also enjoy picturesque views of the city's skyline along the scenic riverfront. The city's shopping options are equally impressive, with a wide range of boutiques and department stores. Chicago's unique blend of art, culture, and entertainment ensures a memorable family vacation.

  • Travelers tend to stay 2 days in Chicago

2. Book your ideal Galena with a vacation package

Galena, Illinois is a charming destination for outdoor enthusiasts. Its picturesque location along the river and hilly terrain make it ideal for activities like hiking, biking, and boating. History buffs will enjoy exploring the town's museums and historical sites, while wine lovers can indulge in tastings at local wineries. For those seeking a bit of excitement, the nearby casino offers entertainment and gaming options. Galena is also known for its friendly people and vibrant shopping scene, with unique boutiques and antique shops. With a mix of natural beauty and cultural attractions, Galena has something for everyone.

  • Travelers tend to stay 2 days in Galena

3. Enjoy Schaumburg with a travel package

Champaign, Illinois is a vibrant city with a diverse and lively atmosphere. Located near the University of Illinois, it offers a rich cultural experience with its thriving theater and live music scene. Visitors can enjoy a wide range of entertainment options, from sports events to opera performances. The city also boasts excellent dining and shopping opportunities, catering to all tastes and preferences. Whether you're a fan of football or looking for family-friendly activities, Champaign has something for everyone. Soak up the local atmosphere and immerse yourself in the vibrant culture of this charming Midwestern city.

  • The peak season is from May to July
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Schaumburg

4. Plan your dream getaway to Rosemont

Rosemont, Illinois is the perfect destination for a family vacation. With its close proximity to Chicago, there are endless opportunities for entertainment and fun. Whether you're a sports fan looking to catch a hockey game, a shopaholic in search of the latest fashion trends, or a foodie looking to indulge in delicious dining options, Rosemont has it all. The town offers a variety of outdoor activities such as biking and recreation, as well as theaters and live music venues for those seeking cultural experiences. With its vibrant atmosphere and diverse range of attractions, Rosemont is guaranteed to provide a memorable family vacation.

  • The peak season is from July to September
  • The off-peak season is from October to December
  • Travelers tend to stay 2 days in Rosemont

6. Escape to Springfield with a vacation package

Springfield, Illinois is a perfect destination for a family vacation. The city offers a diverse range of activities and attractions suitable for all ages. Explore the numerous museums and historical sites, such as the Abraham Lincoln Presidential Library and Museum. Enjoy live music performances and take part in the lively festivals held throughout the year. The city's architecture and shopping scene are also worth exploring. Springfield provides a family-friendly atmosphere with plenty of dining options to satisfy everyone's taste buds. Whether you're interested in history, culture, or simply having a good time, Springfield has something for everyone.

  • Travelers tend to stay 2 days in Springfield

5. Explore Naperville with a vacation package

Schaumburg, located in Illinois, offers a diverse range of experiences for family vacations. The town is known for its excellent shopping and dining options, as well as its sports and football facilities. Families can enjoy a variety of family-friendly activities and entertainment, such as horseback riding and live music. The friendly people and the vibrant atmosphere make Schaumburg a welcoming destination for travelers. Whether you're looking to explore the local attractions or simply relax and enjoy the local atmosphere, Schaumburg has something to offer for everyone.

  • The peak season is from May to July
  • The off-peak season is from October to December
  • Travelers tend to stay 2 days in Naperville

Illinois Hotel Deals

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
$168 nightly
The price is $198 total per night from Sep 3 to Sep 4
$198 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."

Reviewed on Aug 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $200 total per night from Sep 1 to Sep 2
$200 total
Sep 1 - Sep 2
Total with taxes and fees
Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
$155 nightly
The price is $182 total per night from Sep 2 to Sep 3
$182 total
Sep 2 - Sep 3
Total with taxes and fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 10,138 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.
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Frequently asked questions

How much does an Illinois vacation package cost?
Perhaps much less than you think — from a low $409, actually! By combining hotels, flights and car rentals into a tailor-made vacation package, your Illinois escape is just clicks away.
How do I get a cheap travel package to Illinois?
Booking a flight and hotel together with Expedia won't just save precious time — it'll save you a nice amount too. An Illinois vacation package makes it simple to put together your perfect trip. With more than 550 airlines throughout the world to choose from, finding convenient flights that suit your schedule won't be a problem. In addition to that, we have over 1,000,000 properties globally to choose from. Now that's choice! No matter who you are, Expedia brings the world within your reach.
Where should I stay in Illinois?
If you want to explore popular sights such as Wrigley Field and Six Flags Great America, head straight for Chicago. Stay a few extra nights to really look around this thriving city.
What are the top hotels in Illinois?
When it comes to hotels in Chicago, River Hotel and Embassy Suites by Hilton Niagara Falls Fallsview are a couple of favorites. If you're also spending time in Galena, Aloft Chicago Mag Mile and Motel 6 Elk Grove Village, IL - O'Hare look forward to welcoming you.
How far in advance should I book my Illinois vacation?
Browse Expedia to compare international fares ASAP. You can normally purchase a ticket up to a year in advance. If you don't see your preferred air carrier, or you've left things to the last moment, don't despair. Cheap fares to Illinois sometimes occur within weeks of the date of departure.
What does an Expedia Illinois travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to create your ideal Illinois package. Once you've made your booking, you can add on fun stuff like sightseeing tours and activities. Remember, the more you bundle, the more dollars you'll save!
What should I know before booking an Illinois travel package?
Whether it's adventure or relaxation you're seeking, an Illinois vacation package lets you plan your escape your way. Plus, you'll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with an Illinois Expedia vacation package?
Yes, you're in charge. We have access to over 550 partner airlines worldwide, so you can design your Illinois trip according to your needs and budget.
Does Expedia offer Book Now, Pay Later Illinois vacation packages?
If you'd prefer to spread the cost of your hotel and flight over a number of installments, Expedia is here to help. Paying the total cost of your trip upfront isn't always the best way to budget for your vacation, so we've joined forces with online lender Affirm to give you financial freedom. Book Now, Pay Later and take the stress out of saving to travel.
If I'm not able to travel, can I cancel my Illinois vacation package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can cancel or change your Illinois vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for further details.

Discover the most popular places to visit in Illinois

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Illinois

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Illinois
Explore a world of travel with Expedia

Explore a world of travel with Expedia

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.