How much does a Chicago vacation package cost?

You'll find cheap prices from $484 on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chicago costs.

What are the cheapest months to go to Chicago?

You can generally find lower prices and greater availability in December, January and February. Explore our cheap Chicago vacation packages and you could score some excellent off-season deals.

How many days is enough for Chicago?

To fully enjoy a Chicago vacation, we suggest staying for 2 days. Divide your time between visiting Shedd Aquarium , Chicago Theatre and other leading sights, on top of exploring neighborhoods like Central Chicago and Magnificent Mile. If you've got some time to spare, include a day trip or tour in your Chicago vacation itinerary.

Is it worth booking a vacation package to Chicago?

Chicago has everything you need for an awesome break — culture, views and dining are just the start. Whether you want to visit sights such as Millennium Park and Art Institute of Chicago , or venture off the beaten track, you'll find plenty to explore on your Chicago vacation.

How to find the best Chicago package deals?

Use Expedia's filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.

Is it cheaper to book a Chicago vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a customized Chicago vacation by choosing your favorite accommodation type, airline and car class.

When to book a vacation package to Chicago?

Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.

How to plan a trip to Chicago?

Choose your dates: What you'd like to do in Chicago and your favorite season can help you decide when to go. Set your budget: Consider costs like flights, food and transportation when calculating how much to put aside for your trip to Chicago. Then, pick a property that works with your budget, whether that's a wallet-friendly stay or a high-end retreat. Organize your Chicago escape with our trip planning tool : Look for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Chicago together. Decide how long to go for: Now that you're up to speed on Chicago, you can work out the ideal length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to do. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Chicago vacation package. Add on experiences and excursions: Take a look at our dedicated travel guide to find some awesome things to do in Chicago . Book tickets or make reservations in advance to save time and avoid the hassle of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Chicago vacation packages?

Jet off on your dream getaway to Chicago with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for the next payday — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snag great deals before they disappear.

Chicago Vacation Packages 2025/2026 from $484

Your Chicago getaway

With a multitude of well-known landmarks and vibrant neighborhoods to explore, Chicago promises an unforgettable vacation. Discover accommodations in downtown Chicago, offering access to top-tier dining, cultural hotspots, and captivating entertainment. From Millennium ParkOpens in a new window to the Art Institute of ChicagoOpens in a new window, design your perfect itinerary and make unforgettable memories with ease through Expedia.

The Latest Chicago vacation packages

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

The Royal Sonesta Chicago River North

Downtown Chicago

$484

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,980 reviews)

Friendly staff, clean and comfortable, convenient location

Reviewed on Aug 20, 2025

Hotel Riu Plaza Chicago

Downtown Chicago

$658

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,270 reviews)

Great experience, highly recommended.

Reviewed on Aug 21, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Save 100% on your flight

$494

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (1,925 reviews)

Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.

Reviewed on Aug 20, 2025

The Emily Hotel

Downtown Chicago

$807

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,159 reviews)

Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on Aug 17, 2025

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

$857

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on Aug 17, 2025

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Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

Chicago Hotel Deals

The Wade

644 N Lake Shore Dr, Chicago, IL

Fully refundableReserve now, pay when you stay

$151 nightly

$177 total

Sep 1 - Sep 2

Total includes taxes and fees

8.2/10 Very Good! (1,207 reviews)

"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on Aug 20, 2025

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Fully refundableReserve now, pay when you stay

$136 nightly

$160 total

Aug 24 - Aug 25

Total includes taxes and fees

7.8/10 Good! (8,965 reviews)

"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on Aug 17, 2025

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

$161 nightly

$189 total

Sep 3 - Sep 4

Total includes taxes and fees

8.4/10 Very Good! (4,729 reviews)

"The hotel was wonderfully nestled downtown and an easy walk to sites and restaurants."

Reviewed on Aug 18, 2025

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.

Things to do in Chicago

Chicago offers a vibrant mix of family-friendly activities and outdoor adventures, making it perfect for a city-themed vacation. Visitors can explore popular shopping districts, enjoy thrilling sporting experiences, and visit iconic attractions. Don't miss out on free outdoor attractions that highlight the city's charm. Whether you're planning a day trip or seeking educational opportunities, Chicago has something for everyone to enjoy.

Shopping

In Chicago, Woodfield Mall offers a vibrant shopping experience with entertainment and family-friendly options. For unique gifts, visit the LEGOLAND® Discovery Center. Additionally, Chicago Place Mall features a mix of shops in a bustling city atmosphere, perfect for finding souvenirs to remember your trip.

Recreation

At Wrigley Field, immerse yourself in the electric atmosphere of a Chicago Cubs game, perfect for sports enthusiasts. The Chicago Theatre offers a captivating experience with its stunning architecture and diverse performances, while the Aragon Ballroom provides an entertaining backdrop for live music events, ideal for a night out.

Adventure

Experience the thrill of the Great Wolf Lodge Water Park, featuring exhilarating slides and wave pools perfect for family fun. For arcade excitement, head to Galloping Ghost, where classic games await. Enjoy nature at Salt Creek Trail, offering scenic hiking paths amidst beautiful outdoor surroundings.

Nightlife

Experience Chicago's vibrant nightlife at places like Dave & Buster's for a fun pub atmosphere. Enjoy live music and romance at Kingston Mines and Blues on Halstead, both offering a lively city vibe. These venues promise an unforgettable night filled with entertainment and good company.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Chicago

Chicago is a fantastic destination for families and outdoor enthusiasts, offering a blend of urban parks, beautiful beaches, and modern universities. Visitors can immerse themselves in the city's rich culture while exploring iconic attractions like the Chicago River and the scenic Riverwalk. Whether you're looking for a city-themed vacation or a family-friendly experience, Chicago has something to offer everyone.

Navy Pier: Experience the vibrant atmosphere of Navy Pier, a bustling hub of entertainment and relaxation. With stunning views of Lake Michigan, you can enjoy attractions like the Ferris wheel, gardens, and local shops, all while soaking in the friendly local vibe.
Michigan Avenue: Stroll along Michigan Avenue, often referred to as the Magnificent Mile. This iconic street is lined with upscale boutiques, cultural landmarks, and delightful dining options, offering a quintessential city experience that captures the essence of Chicago.
McCormick Place: As the largest convention center in North America, McCormick Place hosts a variety of events and exhibitions. Its state-of-the-art facilities and dynamic atmosphere make it a key destination for business travelers and event-goers alike.

Best time to go to Chicago

The best time to visit Chicago is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly	Average	Slightly Low

Tips to save on your trip to Chicago

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chicago.
Consider traveling to Chicago during the low season (December to February) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.