Chicago Vacations from ¥194,842

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The Latest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont
Hotel Riu Plaza Chicago
Pendry Chicago
DoubleTree by Hilton Chicago - Alsip
Fairmont Chicago at Millennium Park

Where to stay in Chicago

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

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

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥21,592 per night from Feb 14 to Feb 15
¥21,592
¥25,347 total
Feb 14 - Feb 15
includes taxes & fees
8/10 Very Good! (9,826 reviews)
Awesome location

Reviewed on Jan 30, 2026

Congress Plaza Hotel
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
Fully refundableReserve now, pay when you stay
The price is ¥15,865 per night from Feb 8 to Feb 9
¥15,865
¥18,623 total
Feb 8 - Feb 9
includes taxes & fees
8.4/10 Very Good! (5,617 reviews)
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.

Reviewed on Jan 28, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥30,014 per night from Feb 21 to Feb 22
¥30,014
¥35,233 total
Feb 21 - Feb 22
includes taxes & fees
8.2/10 Very Good! (2,187 reviews)
Room was great and so was the service.

Reviewed on Jan 25, 2026

Hilton Chicago O'Hare Airport
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.