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Chicago Holidays

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Where to stay in Chicago

Find the best Chicago areas for the activities you enjoy most. Learn more about Chicago
Learn more about Chicago
A river with yellow boats, a bridge, and tall buildings.

The Loop

The Loop pulses with energy as Chicago's iconic skyline reaches skyward. Art and business collide at every corner, from Cloud Gate's gleaming curves to historic skyscrapers. Experience world-class culture at the Art Institute or Chicago Symphony Orchestra. Named for the elevated train tracks encircling city centre, this area offers excellent transit connections. Millennium Park provides green space amid urban intensity. Weekdays buzz with business crowds while weekends reveal a quieter side of this architectural wonderland.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

River North captivates visitors with America's largest concentration of art galleries outside Manhattan. This upscale Chicago area blends high-end dining with vibrant nightlife along the scenic riverfront. Stunning architecture frames the bustling streets. The area boasts exceptional transit options with three nearby metro stations. Browse through contemporary exhibits, enjoy cocktails at stylish rooftop bars, or shop at luxury boutiques. Merchandise Mart and Bally's Casino offer additional entertainment in this walker-friendly urban playground.

A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

Chicago's famous Magnificent Mile dazzles with luxury shopping and architectural wonders. Michigan Avenue showcases high-end retailers like Bloomingdale's and Neiman Marcus alongside historic landmarks such as the Water Tower. The district seamlessly blends shopping paradise with cultural attractions. Business travellers appreciate the numerous office buildings and hotels lining North Michigan Avenue. Visitors can enjoy fine dining establishments, explore the Chicago Riverwalk, or venture to nearby attractions like Navy Pier and the Art Institute of Chicago. The area's stunning skyline views and riverfront access create an unforgettable urban experience.

A cityscape with modern skyscrapers and a curved highway.

West Loop

West Loop has transformed from industrial roots into Chicago's trendiest food destination. Old warehouses now house sleek restaurants along "Restaurant Row" where celebrity chefs create culinary magic. Art galleries and design studios fill converted brick buildings throughout this vibrant area. Union Park and Mary Bartelme Park offer green retreats amid the urban landscape. Getting around is simple with multiple train stations including Racine and Clinton. The area balances its industrial heritage with modern luxury in this walkable food lover's paradise.

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Lincoln Park blends urban energy with natural beauty along Chicago's stunning lakefront. The neighborhood's namesake 1,200-acre park offers endless recreation with a free zoo, conservatory, and scenic trails. Historic brownstones line tree-canopied streets, creating a charming residential atmosphere. Visitors can shop unique boutiques along Armitage Avenue or enjoy diverse dining options on Clark Street. The Chicago History Museum and North Avenue Beach provide cultural and outdoor attractions. Three convenient metro stations make exploring the rest of the city a breeze.

Discover the most popular places to visit in Chicago

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."

What to do in Chicago

360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
See all activities in Chicago

Chicago Hotel Deals

Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
2.2 km from Chicago (and vicinity)
9.0 out of 10, Wonderful, (4,603 reviews)
"The location of this place is perfect, and the room was spacious and extremely comfortable. The main area for improvement is housekeeping. My daughter came down with a terrible cold, so I left the sign requesting room service. They made the bed using the same dirty, stained sheets instead of replacing them. Housekeeping also did not dust the bedside tables or any of the furniture, nor did they vacuum the floors."
The price is S$269
includes taxes & fees
16 Aug - 17 Aug
Hilton Chicago/Magnificent Mile Suites
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.
See all properties in Chicago

Frequently Asked Questions

How much does a Chicago holiday package cost?

You'll find cheap prices 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.

Book with confidence

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.

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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.