Chicago Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Chicago Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Omni Chicago Hotel
Level Chicago – Old Town
Trump International Hotel & Tower Chicago
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

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$187 per night from 6 Jul to 7 Jul
S$187
6 Jul - 7 Jul
includes taxes & fees
8/10 Very good! (10,139 reviews)
"Very cool old hotel in a great location. Well-restored and comfortable. Bell captains were very helpful with suggestions for local attractions and cabs."

Reviewed on 2 Jul, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$278 per night from 5 Jul to 6 Jul
S$278
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,834 reviews)
"We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay."

Reviewed on 2 Jul, 2026

Omni Chicago Hotel
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$333 per night from 4 Jul to 5 Jul
S$333
4 Jul - 5 Jul
includes taxes & fees
8.4/10 Very good! (2,336 reviews)
"I have severe mobility issues, but was taken by wheelchair directly from United gate to Hilton reception desk. Restaurants were close to reception and elevators, so accessible with stroller."

Reviewed on 2 Jul, 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.

Stay near popular Chicago attractions

What to do in Chicago

Frequently asked questions

How much does a Chicago holiday package cost?
You'll find cheap prices from S$554 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 holiday 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 holiday packages. Opting to travel in quieter periods means you'll typically find lower prices on accommodation and flights.
How many days is enough for Chicago?
To fully enjoy a Chicago holiday, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighbourhoods like Central Chicago and Near North Side. If you've got some spare time, include a day trip or tour in your Chicago holiday itinerary.
Is it worth booking a holiday 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 holiday.
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 holiday package well in advance.
Is it cheaper to book a Chicago holiday as a package?
Expedia holiday 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 customised Chicago holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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 holiday 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. 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.