Chicago Holidays
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Where to stay in Chicago
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.
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.
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.
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.
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
Wrigley Field
Soldier Field
What to do in Chicago
Skydeck Chicago at Willis Tower
Chicago Hotel Deals
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton"Staff is greatly appreciated and the room is very clean"
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago"Great location from both airports. Lovely hotel clean and convenient"
"Amazing location, great property"
"I have been to Chicago many times, but this is the first time at the Hyatt Regency. From the staff to the amenities it was outstanding!!! Highly recommend staying here if you are planning on coming to this wonderful city!"
Hyatt Place Chicago/River North
Hyatt Place Chicago/River North"Clean, friendly staff, and nice location."
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHGFind out more about Chicago
Things to do in Chicago
Chicago is an excellent destination for family getaways, outdoor adventures, and city-themed holidays. Visitors can enjoy a variety of activities, including vibrant shopping areas, thrilling arena entertainment, and captivating theatre performances. Key highlights include engaging city tours, attending a Cubs game, indulging in outdoor fun, and experiencing live music that showcases the city's rich culture and entertainment options.
Shopping
Woodfield Mall offers a vibrant shopping experience with a mix of business and family entertainment. For a fun twist, visit LEGOLAND® Discovery Center, perfect for children. Additionally, Chicago Place Mall provides a delightful city atmosphere, ideal for family outings and shopping for unique gifts.
Recreation
At Wrigley Field, immerse yourself in the exhilarating atmosphere of live sports, perfect for energising your spirit. The Aragon Ballroom offers vibrant musical performances, creating a lively and entertaining experience, while the Riviera Theatre enchants with its romantic and cultural vibes, ideal for a memorable evening out.
Adventure
Experience the excitement at Kiddie Kingdom, an arcadeAdventureZone filled with fun for the whole family. Dive into the thrilling attractions at Great Wolf Lodge Water Park, where adventure and entertainment await. For a serene escape, explore Salt Creek Trail, a picturesque hikingTrail surrounded by nature's beauty.
Nightlife
In Chicago, experience vibrant nightlife at venues like Dave & Buster's, where you can enjoy drinks and entertainment. Kingston Mines and Blues on Halstead offer lively atmospheres with romance and city vibes, perfect for dancing and live music in a dynamic urban setting.
Find the best attractions in Chicago
Chicago offers a delightful experience for families and outdoor enthusiasts, featuring urban parks, modern colleges, and event venues. This vibrant city caters to those seeking cultural immersion and family-friendly activities. Be sure to explore downtown Chicago, where you can discover a myriad of attractions and events that capture the essence of city life. Enjoy your visit to this dynamic metropolis.
- Michigan Avenue: Experience the vibrant heart of Chicago along Michigan Avenue, known for its stunning architecture, luxury shopping, and bustling atmosphere. This iconic street is the perfect place to immerse yourself in the city's energy and artistry.
- Navy Pier: Enjoy the scenic beauty and urban charm of Navy Pier, where you can stroll along the waterfront, indulge in local cuisine, and participate in various entertainment options. With its friendly vibe, it's an ideal spot for families and friends alike.
- Millennium Park: Discover the lush greenery and artistic installations of Millennium Park, a family-friendly urban oasis. Relax outdoors amidst the stunning city skyline while enjoying various cultural events and public art displays.
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.
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?
- 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.
- 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.
- 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.
- 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.