Chicago Holidays

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The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.

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

Chicago offers a delightful blend of family-friendly activities and vibrant city life. Enjoy thrilling city tours, catch a Cubs game, and explore outdoor fun in the city's parks. Don't miss the opportunity to experience live music and immerse yourself in the local theatre scene. With its bustling shopping areas and entertainment facilities, Chicago promises an unforgettable vacation filled with diverse adventures for everyone.

Shopping

At Woodfield Mall, you can indulge in a vibrant shopping experience with a variety of shops and entertainment options. For a unique twist, visit the LEGOLAND® Discovery Center, perfect for families. Don’t miss Oakbrook Center Mall, offering a blend of shopping and leisure in a charming setting.

Recreation

Wrigley Field offers an electrifying atmosphere for sports enthusiasts, perfect for soaking up the local vibe. For a touch of culture and romance, Harris Theater showcases captivating performances. Meanwhile, Chevy Chase Country Club provides a luxurious retreat with exceptional amenities, ideal for relaxation and leisure.

Adventure

Xtreme Trampolines is an exhilarating arcadeAdventureZone in Chicago, offering a vibrant atmosphere perfect for family fun. Great Wolf Lodge Water Park promises thrilling water slides and entertainment for all ages. For a scenic adventure, explore the Salt Creek Trail, a picturesque hikingTrail surrounded by nature.

Nightlife

Chicago's nightlife is vibrant and diverse. Enjoy a fun evening at Dave & Buster's, where romance meets entertainment in a lively pub atmosphere. For a taste of the city's rhythm, Kingston Mines and Blues on Halstead offer energetic nightclubs, perfect for immersing yourself in live music and city vibes.

*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 vibrant urban experience. Visitors can explore urban parks, modern colleges, and event venues that reflect the city's rich culture. Attractions cater to those seeking a blend of family-friendly activities and city exploration. Don't miss the chance to enjoy the lively atmosphere of downtown Chicago, where a plethora of dining, shopping, and cultural experiences await.

  • McCormick Place: As the largest convention centre in North America, McCormick Place offers a vibrant atmosphere for business events and exhibitions. Its modern architecture and diverse facilities create a unique setting where you can engage with various industries and innovative ideas.
  • Millennium Park: A stunning urban oasis in the heart of Chicago, Millennium Park is perfect for families and outdoor enthusiasts. Enjoy iconic attractions like the Cloud Gate sculpture and the Jay Pritzker Pavilion, while participating in events and enjoying the lush gardens.
  • Six Flags Great America: This exhilarating theme park provides endless entertainment for families. With thrilling rides, engaging shows, and a variety of attractions, it’s an ideal destination for adventure seekers looking to create lasting memories.

Best time to go to Chicago

The best time to visit Chicago can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chicago falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chicago falls in January, 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 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.

Top hotels in Chicago

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 S$132 per night from 16 Feb to 17 Feb
S$132
16 Feb - 17 Feb
includes taxes & fees
8/10 Very Good! (9,881 reviews)
Great location, beautiful historic hotel with clean, updated rooms.

Reviewed on 11 Feb, 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 S$211 per night from 4 Mar to 5 Mar
S$211
4 Mar - 5 Mar
includes taxes & fees
9.2/10 Wonderful! (3,295 reviews)
Everything was amazing, specially the breakfast buffet.

Reviewed on 7 Feb, 2026

Hotel Riu Plaza Chicago
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 S$290 per night from 14 Mar to 15 Mar
S$290
14 Mar - 15 Mar
includes taxes & fees
8.2/10 Very Good! (2,211 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.

Reviewed on 2 Feb, 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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What to do in Chicago

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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.