Chicago Holidays

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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

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 S$171 per night from 25 May to 26 May
S$171
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,651 reviews)
Rooms were infrequently cleaned and we had to request soap and new towels (no we didn’t have our (no housekeeping) sign up). Other than that it was a nice stay.

Reviewed on 1 May, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$205 per night from 26 May to 27 May
S$205
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,140 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it

Reviewed on 29 Apr, 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundable
The price is S$166 per night from 26 May to 27 May
S$166
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (3,464 reviews)
Great check in and check out experience

Reviewed on 29 Apr, 2026

Club Quarters Hotel, Central Loop, 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.

Popular places to visit

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.