Chicago Hotels from S$101

Top reasons to visit Chicago

• Iconic Architecture: Chicago is renowned for its stunning skyline, featuring architectural marvels such as the Willis Tower and the John Hancock Centre.
• Cultural Richness: Experience the city's vibrant arts scene with world-class theatres, galleries, and live music performances.
• Beautiful Parks and Beaches: Enjoy scenic strolls along the waterfront and relax in urban parks like Millennium Park.
• Diverse Neighbourhoods: Explore the unique character and charm of Chicago's various neighbourhoods, each offering a distinct atmosphere.
• Family-Friendly Attractions: Discover countless activities perfect for families, from museums to interactive experiences.

Find great hotels in Chicago

Discover a range of exceptional accommodations in Chicago, where comfort meets style. Our hotels cater to diverse needs, offering facilities for business travellers, pet-friendly options, and a welcoming atmosphere for the LGBTQIA community. Whether you're seeking a luxurious stay or a cosy apartment, Chicago's top hotels promise a memorable experience for all visitors.

• Congress Plaza Hotel: This 3.5-star hotel exudes a classic charm, perfectly catering to business and leisure travellers alike. Located in the heart of Chicago's shopping district, it offers easy access to an array of retail options. Guests appreciate the spacious accommodations and the hotel’s historic ambience, with amenities that include a fitness centre and meeting facilities. The hotel is an ideal choice for those seeking a blend of convenience and a touch of elegance during their stay in the Windy City.
• Best Western Grant Park Hotel: This budget-friendly option is particularly suitable for families, with a guest rating of 8.2 out of 10. The hotel provides thoughtful amenities for children, such as free cribs and safety features like window guards. Located in the vibrant shopping district of Chicago, it offers easy access to family-friendly attractions. Guests commend the comfortable rooms and the warm, welcoming atmosphere, making it an excellent choice for families looking to explore the city while keeping costs manageable.
• LondonHouse Chicago, Curio Collection by Hilton: A luxurious 4.5-star retreat, LondonHouse offers an upscale experience with a focus on relaxation and indulgence. This hotel features a full spa, complete with a variety of treatments, including aromatherapy and prenatal massages, ensuring guests can unwind after exploring the city. Its prime location in the shopping district enhances its appeal for those keen on retail therapy. The stunning rooftop terrace provides breathtaking views of the Chicago skyline, making it a standout destination for travellers seeking both luxury and leisure.

Where to stay in Chicago

Chicago offers an exciting blend of urban vibrancy and scenic charm, perfect for families and city explorers alike. Discover the lively downtown, where iconic architecture meets rich culture, and wander through diverse neighbourhoods that showcase an authentic Chicago experience. From romantic strolls along the waterfront to family-friendly attractions, this metropolis invites you to immerse yourself in its warm atmosphere and friendly locals, ensuring an unforgettable adventure in the Windy City and its charming surroundings.

• Downtown Chicago: The vibrant heart of Chicago, Downtown is known for its iconic skyline, bustling streets, and rich cultural offerings. Visitors can immerse themselves in a city-themed experience, with a plethora of shopping options, world-class theatres, and thrilling arena entertainment. Key landmarks include Millennium Park, the Art Institute of Chicago, and sports venues like the United Center. The area's urban parks provide a refreshing retreat amidst the city's hustle, making it an ideal spot for families seeking outdoor activities.
• Arlington Heights: Situated just north of Chicago, Arlington Heights is a charming city that blends suburban tranquillity with urban conveniences. Known for its family-friendly atmosphere, the city attracts visitors for both leisure and business. Popular venues include the bustling shopping malls and theatres, while landmarks such as the Arlington International Racecourse and convention centres host various events throughout the year. Arlington Heights offers a pleasant escape from the city, with a welcoming community vibe and ample recreational opportunities.
• Schaumburg: Located to the northwest of Chicago, Schaumburg is a bustling city that serves as a hub for shopping and entertainment. Visitors are drawn to its family-oriented attractions, including the expansive Woodfield Mall and numerous theatres. The city is also home to significant business venues, such as the Renaissance Schaumburg Convention Center. With a range of dining options and parks, Schaumburg offers a delightful mix of city and suburban experiences, making it an excellent stop for travellers looking to explore the Chicago area.

Things to do in Chicago

Shopping

Only a short distance from the Magnificent Mile, the Water Tower Place offers a mix of high-end brands and unique boutiques. For a more local feel, explore the bustling Lincoln Park Farmers Market, where you can find artisanal goods and charming souvenirs.

Recreation

In Chicago, the Peninsula Spa offers a serene retreat with a range of rejuvenating treatments and a tranquil relaxation area. Nearby, the Holistic Health Centre provides yoga classes and wellness workshops, creating an inviting space for mindfulness and personal growth amidst the city's vibrant atmosphere.

Adventure

The Chicago River offers thrilling kayak tours, allowing you to paddle through the city’s stunning architecture. For a unique view, try the Skydeck at Willis Tower, where you can step onto a glass ledge suspended 1,353 feet above the ground for an exhilarating experience.

Nightlife

Explore the vibrant nightlife at The Aviary, where innovative cocktails meet stunning views. For a more laid-back atmosphere, visit the Green Mill Cocktail Lounge, a historic jazz club offering live performances that transport you to a bygone era. Enjoy the unique charm each venue presents.

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 ideal for family, outdoor, and city-themed holidays, boasting a variety of attractions. Visitors can enjoy urban parks, stunning beaches, and iconic skyscrapers while immersing themselves in the city's rich culture and family-friendly experiences. Whether you're seeking adventure or cultural enrichment, Chicago's diverse points of interest promise an unforgettable getaway.

• Grant Park: This expansive urban park in the heart of Chicago offers a serene escape with its lush green spaces, vibrant flower beds, and iconic statues. Known as Chicago's front yard, it hosts numerous events and festivals, making it a lively gathering spot for families and tourists alike.
• Chicago Riverwalk: A picturesque promenade along the Chicago River, the Riverwalk invites visitors to enjoy scenic views, dining options, and recreational activities. This family-friendly area is perfect for leisurely strolls, boat tours, and enjoying the vibrant atmosphere of the city.
• Michigan Avenue: Renowned as the Magnificent Mile, this bustling street is a hub of shopping, dining, and cultural attractions. Visitors can explore high-end boutiques and iconic landmarks while soaking in the dynamic city vibes that characterise Chicago.

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.

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

Reaching Chicago is convenient with its major airports. Chicago O'Hare International Airport (ORD) is situated 25.7km from the city centre, with notable hotels nearby such as the 4.5-star Loews Chicago O'Hare Hotel and the Hyatt Regency O'Hare Chicago, both 3.2km away. Midway International Airport (MDW), located 14.5km from downtown, offers luxurious options like the 5-star Trump International Hotel & Tower Chicago and Nobu Hotel Chicago. For those considering Milwaukee General Mitchell International Airport (MKE), it is 120.7km away, with excellent hotels such as the Potawatomi Hotel & Casino, just 9.7km from the airport.