Chicago Vacations from ¥280,988

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The Latest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Hotel Riu Plaza Chicago
Swissotel - Chicago
Trump International Hotel & Tower Chicago
LondonHouse Chicago, Curio Collection by Hilton

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 ¥21,260 per night from May 25 to May 26
¥21,260
¥25,274 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (10,134 reviews)
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."

Reviewed on May 23, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥38,046 per night from Jun 16 to Jun 17
¥38,046
¥49,771 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,221 reviews)
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly ..."

Reviewed on May 24, 2026

Hotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥13,817 per night from May 25 to May 26
¥13,817
¥21,285 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,717 reviews)
"Too small room no refrigerator no microwave over prized vallet parking when they park in open public parking space which cost less."

Reviewed on May 23, 2026

Hotel Felix River North/Magnificent Mile
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.