Chicago Vacations from ¥274,160

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The Latest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥274,160
per person
Nov 6 - Nov 9
found 7 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The property waa clean and spacious Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that A Garrett's popcorn shop waa right across the street!

Reviewed on Aug 11, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥308,437
per person
Nov 6 - Nov 9
found 7 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Sentral Michigan Avenue

Sentral Michigan Avenue

Downtown Chicago
¥494,270
per person
Sep 14 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,237 reviews)
Great value. Right on Michigan Ave. front desk staff very helpful.

Reviewed on Aug 11, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥360,552
per person
Sep 18 - Sep 22
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Freehand Chicago

Freehand Chicago

Downtown Chicago
¥279,254
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.8/10 Good! (3,233 reviews)
The overall property is dark and the carpets and walls on the hotel floors are dirty. My room also had dirty walls and a dirty shade that did not work well. While the sheets were seemingly clean, as was the bathroom, I was hesitant to walk in bare feet on the carpet. One of the two elevators was always broken down pretty much my entire stay. I prepaid for the week so I had to tough it out, but I will not be back.

Reviewed on Aug 10, 2026

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Find the Best Chicago Vacation Packages

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly 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

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
¥16,474
¥19,588 total
Sep 8 - Sep 9
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
¥22,555
¥26,816 total
Aug 31 - Sep 1
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
¥35,605
¥41,797 total
Sep 5 - Sep 6
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 5,375 properties in Chicago
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.
Photo by © City of Chicago

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."
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A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)
This historic Chicago waterfront landmark offers panoramic lake views from its iconic Centennial Wheel. Enjoy seasonal fireworks or interactive exhibits at the Children's Museum while exploring Navy Pier.
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A large stadium surrounded by a cityscape with modern buildings.
Photo by © City of Chicago

Soldier Field

8.8/10 (7,063 reviews)
Soldier Field blends historic neoclassical columns with modern design as home to the Chicago Bears. Experience the electric atmosphere of an NFL game or take a guided tour exploring its century of sporting heritage.
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A modern cityscape with tall buildings, a clear sky, and a tree-lined street.
Photo by © Cesar Russ Photography

McCormick Place

8.8/10 (9,822 reviews)
McCormick Place hosts major events like the Chicago Auto Show in its 2.6 million square feet of exhibition space. Arrive via the convenient Metra Electric Line station directly beneath the complex.
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A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 reviews)
This 1.25-mile urban promenade showcases Chicago's stunning architecture alongside the river. Stroll past public art installations, dine at waterfront cafés, or catch the evening Art on theMART digital projection show.
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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)
Discover Chicago's artistic heart at Millennium Park, home to the reflective Cloud Gate and interactive Crown Fountain. Stroll through Lurie Garden or catch a free concert at the Jay Pritzker Pavilion.
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A roller coaster in motion against a clear blue sky.

Six Flags Great America

8.6/10 (992 reviews)
This Midwest thrill-seeker's paradise boasts 15 roller coasters and immersive themed areas. Arrive at opening to conquer popular rides, or consider a Flash Pass to maximize your adventure.
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What to do in Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Chicago

Frequently asked questions

How much does a Chicago vacation package cost?
You'll find cheap prices from ¥274,160 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

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