How much does a Chicago vacation package cost?

You'll find cheap prices from ￥303,301 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?

December, January and February are the best times to look for cheap Chicago vacation packages. Opting to travel in quieter periods means you'll typically find lower prices on accommodations and flights.

How many days is enough for Chicago?

To fully enjoy a Chicago vacation, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue , Chicago Riverwalk and other well-known attractions, on top of experiencing neighborhoods like Central Chicago and Near North Side. If you've got some spare time, 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 a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field , or take the road less traveled, you'll find plenty to do 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 when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago. Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that's an affordable stay or a swankier getaway. Work out your trip length: Consider how long you'd like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you're interested in without rushing. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chicago vacation package that brings all your bookings together.

Chicago Vacation Packages 2026 from ￥303,301

The Latest Chicago Vacation Packages

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

Hotel Riu Plaza Chicago

Downtown Chicago

￥303,301

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (4,586 reviews)

salty breakfast

Reviewed on Jul 15, 2026

Omni Chicago Hotel

Downtown Chicago

￥334,033

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,819 reviews)

Staff was fantastic and always ready to help; from the front door to the room door!

Reviewed on Jul 15, 2026

Level Chicago Fulton Market

Downtown Chicago

￥309,262

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (512 reviews)

We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on Jul 14, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

￥420,151

per person

Aug 25 - Aug 29

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (2,566 reviews)

Very clean nice workers and amazing views

Reviewed on Jul 14, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

￥380,056

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.6/10 Exceptional! (1,910 reviews)

We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good! All in all, a very happy experience.

Reviewed on Jul 14, 2026

Where to stay in Chicago

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

Things to do in Chicago

Shopping

Your shopping experience in Chicago will be delightful. Visit Woodfield Mall for a variety of shops and entertainment options. Don't miss LEGOLAND® Discovery Center for unique gifts. Gurnee Mills offers great shopping with family-friendly vibes, ensuring a memorable experience as you explore this vibrant city.

Recreation

At Wrigley Field, immerse yourself in the energetic atmosphere of a baseball game and enjoy the lively sports community. For a touch of culture, the Chicago Theatre offers a captivating mix of performances that resonate with romance and family entertainment, perfect for a night out.

Experience the vibrant music scene at the House of Blues Chicago, where you can enjoy live concerts in a lively setting, surrounded by the rich sounds of various genres that promote relaxation and enjoyment.

Adventure

Experience the thrill of Pirates Cove Children's Theme Park with its arcadeAdventureZone, perfect for family fun. Splash into excitement at Rainbow Falls Waterpark, where adventure and entertainment await. For a scenic outdoor escape, hike the Salt Creek Trail and immerse yourself in Chicago's beautiful landscapes.

Nightlife

Experience the vibrant nightlife in Chicago at Blues on Halstead, a lively nightclub offering romance and entertainment. For a fun twist, visit Dave & Buster's, a drinking pub perfect for games and drinks. Don't miss Kingston Mines, another energetic nightclub brimming with city vibes and live music.

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

Find the best attractions in Chicago

Chicago is an ideal destination for families and outdoor enthusiasts, offering a mix of urban parks, modern universities, and event venues. Visitors can immerse themselves in the city's rich culture while exploring attractions like the iconic Chicago Riverwalk and the scenic Chicago River. Whether you're looking to discover the city's vibrant neighborhoods or enjoy family-friendly experiences, Chicago provides something for every traveler.

Michigan Avenue: Experience the vibrant energy of Chicago along Michigan Avenue, known for its stunning architecture, high-end shopping, and bustling atmosphere. This iconic street offers a perfect blend of urban culture and city excitement.
Navy Pier: Enjoy the urban charm and scenic views at Navy Pier, where you can stroll along the waterfront, indulge in local cuisine, and take part in family-friendly activities. The friendly vibe and beautiful lakefront make it a delightful destination.
Millennium Park: Discover the beauty of Millennium Park, a family-friendly urban oasis featuring stunning art installations, lush gardens, and outdoor concerts. It's a perfect spot for relaxation and enjoying the dynamic city ambiance.

Best time to go to Chicago

The best time to visit Chicago is dependent 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 cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	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	Average	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	Slightly High	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 Cloudy	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 during the off-peak season (typically December to February) for more affordable package holidays to Chicago.
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.

Chicago Hotel Deals

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

￥27,419

￥31,253 total

Aug 4 - Aug 5

includes taxes & fees

8.8/10 Excellent! (2,849 reviews)

"Your security guys are lousy"

Reviewed on Jul 14, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

￥26,591

￥31,616 total

Jul 27 - Jul 28

includes taxes & fees

8.2/10 Very Good! (1,744 reviews)

"Front desk person were very r"

Reviewed on Jul 15, 2026

Omni Chicago Hotel

676 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

￥38,128

￥50,731 total

Jul 26 - Jul 27

includes taxes & fees

9.2/10 Wonderful! (1,913 reviews)

"Staff was fantastic and always ready to help; from the front door to the room door!"

Reviewed on Jul 15, 2026

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.

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.

Wrigley Field

9.0/10 (11,704 reviews)

Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."

See properties