Chicago Hotels from from S$59

Top reasons to visit Chicago

• Stunning City Skyline: Experience breathtaking views of Chicago’s iconic skyline from various vantage points, including the Skydeck.
• Diverse Neighbourhoods: Explore charming neighbourhoods each with its own unique character, offering a friendly urban atmosphere.
• Cultural Attractions: Immerse yourself in rich culture through architectural tours, museums, and live music venues.
• Shopping on Michigan Avenue: Indulge in retail therapy along the famous Magnificent Mile, featuring a range of shops and boutiques.
• Family-Friendly Activities: Enjoy numerous parks, beaches, and family-oriented attractions throughout the city.

Find great hotels in Chicago

Discover a diverse selection of accommodation options in Chicago, ranging from luxurious hotels to charming bed and breakfasts. Whether you're seeking a business-friendly environment, a pet-friendly stay, or a welcoming atmosphere for LGBTQIA travellers, Chicago has it all. Notable choices include the Swissôtel Chicago, Hilton Chicago, and various star-rated luxury hotels, ensuring a memorable experience in the Windy City.

• Congress Plaza Hotel: This 3.5-star hotel embodies a business-centric theme, making it an ideal choice for professionals and travellers seeking a productive stay in the bustling heart of Chicago. The Congress Plaza Hotel offers a variety of business amenities, including a well-equipped Business Centre, multiple meeting rooms, and spacious conference facilities. Located in a vibrant shopping district, it provides easy access to retail and dining options, ensuring that guests can balance work and leisure seamlessly. With its classic architecture and attentive service, this hotel caters to those looking for a sophisticated yet practical lodging experience.
• The Whitehall Hotel, BW Premier Collection: A 4-star boutique hotel, The Whitehall Hotel exudes charm and elegance, appealing to those seeking a unique and pet-friendly experience. Nestled in a lively shopping district, the hotel features thoughtfully designed interiors adorned with distinctive decor and artworks. With a welcoming pet policy that allows dogs onsite, it’s perfect for travellers who wish to bring their furry friends along. The hotel’s emphasis on personalisation and style ensures a memorable stay, complemented by its proximity to boutique shops and dining options.
• Best Western Grant Park Hotel: This family-friendly hotel is an excellent choice for those travelling with children, offering a range of amenities designed to ensure comfort and safety. The Best Western Grant Park Hotel provides free cribs, window guards for children's safety, and a first aid kit for peace of mind. Conveniently situated in the shopping district, guests can explore nearby attractions and stores with ease. The welcoming atmosphere and family-oriented services make it an ideal base for creating lasting memories while enjoying the vibrant city of Chicago.

Where to stay in Chicago

Chicago, a vibrant metropolis, offers an array of experiences for every type of traveller. Explore the stunning city skyline from downtown, indulge in retail therapy along the famed Michigan Avenue, and immerse yourself in the charming neighbourhoods that emanate a friendly, urban atmosphere. Whether you're seeking family-friendly activities or a romantic getaway, Chicago's diverse offerings make it the perfect destination for your vacation.

• Downtown Chicago: Nestled in the heart of Chicago, Downtown is a vibrant neighbourhood that serves as the city's bustling core. It offers a unique blend of family-friendly activities, outdoor experiences, and urban exploration. With a plethora of shopping venues, entertainment arenas, and theatres, there's always something to do. Notable landmarks, including the tourist precinct and various sports facilities, provide visitors with a taste of Chicago's rich culture and sporting spirit. The peak travel months of June to August make it an ideal time to experience outdoor festivals and events, though the charm of Downtown can be enjoyed year-round.
• Magnificent Mile: The Magnificent Mile is a renowned shopping and cultural district located in Chicago's northern section. This bustling neighbourhood is perfect for families and city enthusiasts, offering an array of outdoor activities and attractions. Visitors flock to the area during peak seasons, particularly in March to April and July. With its high-end shopping centres, educational venues, and entertainment facilities, the Magnificent Mile promises an exciting urban adventure. The proximity to key landmarks, including various tourist precincts and sports stadiums, ensures a well-rounded experience for any traveller.
• The Loop: The Loop is Chicago's iconic downtown area, rich in history and cultural significance. It serves as a hub for family activities, outdoor enjoyment, and city exploration. Visitors can immerse themselves in the vibrant atmosphere with numerous shopping areas, theatre performances, and entertainment venues. The Loop's proximity to urban parks and sports facilities makes it a delightful spot for relaxation and recreation. With peak visitor numbers in March to April and July, this neighbourhood showcases the city's dynamic spirit throughout the year.

Things to do in Chicago

Chicago is an ideal destination for families and outdoor enthusiasts, offering a vibrant mix of activities. Visitors can enjoy shopping, explore architectural tours, attend a Cubs game, and experience live music in various venues. The city also boasts numerous hotels and entertainment options, making it perfect for a city-themed holiday. With its rich culture and exciting attractions, Chicago promises a memorable experience for tourists.

Shopping

Experience shopping at Woodfield Mall, a vibrant shopping centre teeming with entertainment options. Visit Cabela's for outdoor gear and gifts. Don't miss Maxwell Street Market, a bustling public market where you can find unique souvenirs amidst the lively city atmosphere.

Recreation

Wrigley Field offers an energetic atmosphere, perfect for sports enthusiasts wanting to immerse themselves in the thrill of live games. For a vibrant evening, the House of Blues Chicago combines live music with delicious food, creating an entertaining and relaxing experience. Northbrook Sports Complex provides a peaceful setting for various recreational activities, ensuring a rejuvenating escape.

Adventure

Experience the thrills at Rainbow Falls Waterpark, where excitement and family fun await. For a scenic adventure, hike the Salt Creek Trail, immersing yourself in the beautiful outdoors. Don't miss the Great Wolf Lodge Water Park for exhilarating water slides and entertainment for the whole family.

Nightlife

Experience the vibrant nightlife in Chicago at the iconic Chicago Theatre, where culture and romance intertwine. For a more adventurous evening, visit Galloping Ghost arcadeAdventureZone, brimming with excitement. Alternatively, enjoy a classy night at the North Shore Center for the Performing Arts, perfect for family-friendly entertainment.

Booking tips and Expedia advantages for Chicago

To save money on your trip to Chicago, consider visiting during the off-peak months of December to February when accommodation prices are lower. Take advantage of the city's free attractions like Navy Pier, Michigan Avenue, and Millennium Park. For transport, opt for walking or using public transport such as trains and buses, which are more economical than taxis. Booking your flights, accommodation, and activities as a package on platforms like Expedia can also yield significant savings. Remember, the cheapest day to stay is Wednesday, while Saturday tends to be the most expensive.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chicago are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chicago is Wednesday. The most expensive day to stay in Chicago is Saturday.
• Find cheap hotels on Expedia: Utilise Expedia’s search tool to tailor your options according to your budget, desired location, and preferred type of accommodation. To discover the most affordable prices and offers, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel accommodation in Chicago with your flights and activities by booking a package through Expedia.

Find the best attractions in Chicago

Chicago is an excellent destination for family, outdoor, and city-themed holidays, offering a variety of attractions such as urban parks, beaches, and modern colleges. Visitors can immerse themselves in rich culture and family-friendly experiences around Central Chicago and enjoy stunning views from the Skydeck. With so much to explore, Chicago promises a memorable vacation for all types of travellers.

• Navy Pier: Experience the vibrant atmosphere of Navy Pier, a scenic jetty that offers stunning views of Lake Michigan. Enjoy leisurely strolls, diverse dining options, and family-friendly attractions, such as the iconic Ferris wheel and the Chicago Children's Museum, all while surrounded by friendly locals.
• Michigan Avenue: Walk along Michigan Avenue, known as the Magnificent Mile, where the city comes alive with its bustling shops, restaurants, and cultural landmarks. This iconic street captures the essence of Chicago's urban vibrancy, making it a must-visit for shopping and entertainment.
• McCormick Place: Discover McCormick Place, the largest convention centre in North America, where business meets innovation. Attend major trade shows and events in this state-of-the-art venue, designed to facilitate networking and collaboration in a dynamic environment.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Average	Slightly Low

The nearest major airports for your trip to Chicago

Arriving in Chicago is convenient with its two primary airports. Chicago O'Hare International Airport (ORD) is situated 25.7km from the city centre, with excellent hotel options nearby, such as the 4.5-star Loews Chicago O'Hare Hotel and the 4-star Hyatt Regency O'Hare, both 3.2km from the airport. The Hilton Chicago O'Hare Airport is an even closer option, just 161m away. Alternatively, Midway International Airport (MDW) lies 14.5km away, with luxurious stays like the 5-star Trump International Hotel & Tower and Nobu Hotel Chicago within easy reach. For those considering South Bend International Airport (SBN), located 614.5km from Chicago, the 4-star Doubletree Hotel South Bend is a notable choice.