How much does a Chicago vacation package cost?

You'll find cheap prices from $866 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 $471

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.

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

per person

Oct 12 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,093 reviews)

The convenience of this location is the only reason to stay here. The rooms are not updated, old bed, no sound proofing, lacking amenities. Disappointing

Reviewed on Aug 1, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

Oct 12 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,635 reviews)

Great stay :) Mr 47 didn’t disappoint

Reviewed on Aug 1, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

per person

Oct 12 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,053 reviews)

Great location. Brand new hotel. The area is hectic and crowded with groups of people who are causing issues. There needs to be more of a police presence. I would expect the area has issues with crime. The area will not reach full potential until they deal with it.

Reviewed on Jul 31, 2025

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Oct 12 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (1,842 reviews)

It never felt like I was at some cookie cutter hotel. Comfortable bed, perfect location for my needs, loved the complimentary coffee in the morning. Will definitely come back the next time I am in town

Reviewed on Aug 1, 2025

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Oct 12 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (3,033 reviews)

Lots of great dining options around the area. The breakfast at the hotel was great.

Reviewed on Jul 29, 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

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Fully refundableReserve now, pay when you stay

$157 nightly

$184 total

Sep 1 - Sep 2

Total includes taxes and fees

7.8/10 Good! (8,938 reviews)

"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug 1, 2025

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

Fully refundable

$236 nightly

$271 total

Sep 1 - Sep 2

Total includes taxes and fees

9/10 Wonderful! (2,150 reviews)

"Loved this hotel. We had a king classic in grand tower high floor. Our bed was comfy, shower was nice, room was large enough and loved the colors. View was decent. Bar had great drinks. Pool is gorgeous. The only negative was the elevators which were compact and wait times were very long sometimes. ..."

Reviewed on Aug 1, 2025

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Fully refundableReserve now, pay when you stay

$144 nightly

$169 total

Aug 17 - Aug 18

Total includes taxes and fees

8.8/10 Excellent! (2,554 reviews)

"Staff friendly, rooms were spacious, very quiet, restaurant was busy but service was still very quick."

Reviewed on Jul 31, 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.