Downtown Chicago Holidays
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Where to stay in Downtown Chicago
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
West Loop
Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
Discover the most popular places to visit in Downtown Chicago
What to do near Downtown Chicago
Skydeck Chicago at Willis Tower
Downtown Chicago Hotel Deals
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Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton"The staff was excellent! The views were amazing and the rooms were clean. The rooftop restaurant/ bar 🎇"
"Gorgeous hotel in a prime location off of the Magnificent Mile. Staff were incredible, buffet breakfast was the perfect way to start our day. My only issue was the amount of air freshener scent throughout the property. It was ok in the lobby but so so strong on our floor leading to our room. It was nauseating. Would definitely stay again and recommend"
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG"I had a great stay at this hotel! The experience was smooth, the room was comfortable, and everything was just what I needed. The staff was friendly, and I would definitely consider staying here again. Highly recommend!"
Find out more about Downtown Chicago
Things to do in and around Downtown Chicago
Downtown Chicago offers a fantastic blend of family-friendly activities and outdoor adventures. Visitors can enjoy vibrant shopping areas, exciting arena entertainment, and captivating theatre performances. A key highlight is the exploration of the Holiday Inn, which provides a comfortable base for your urban getaway. Immerse yourself in the lively atmosphere and cultural richness that this iconic city has to offer.
Shopping
Experience the vibrant shopping scene in Downtown Chicago at the Shops at North Bridge, offering a mix of business and family-friendly vibes. For a local twist, visit Maxwell Street Market, where you can find unique gifts amidst a bustling atmosphere.
Recreation
Soldier Field offers an energetic atmosphere for sports enthusiasts, located a short distance from Downtown Chicago. Harris Theater provides a romantic and cultural experience with diverse performances, while Pritzker Pavilion hosts captivating musical events, adding to the vibrant entertainment scene in the area.
Adventure
Explore Amazing Chicago's Funhouse Maze for an exciting maze adventure filled with optical illusions and surprises. Take a ride on the Centennial Wheel for spectacular views of the city skyline. For a scenic escape, hike along the Salt Creek Trail, surrounded by nature and outdoor beauty.
Nightlife
Experience the vibrant nightlife of Downtown Chicago at Dave & Buster's, where you can enjoy drinks and entertainment in a lively atmosphere. For a taste of the city's rhythm, head to Kingston Mines or Blues on Halstead, both offering romantic vibes and captivating performances just 4.8km away.
Find the best attractions in Downtown Chicago
Downtown Chicago is perfect for family-friendly, outdoor, and city-themed vacations. Visitors can explore iconic skyscrapers, beautiful urban parks, and vibrant streets while enjoying a rich cultural experience. Don't miss the renowned Chicago museums, popular attractions, and the scenic Chicago River, all of which offer a delightful insight into the city's charm and allure.
- Millennium Park: Experience the vibrant atmosphere of Millennium Park, an urban oasis in the heart of Chicago. Enjoy family-friendly events, stunning outdoor art installations, and the iconic Cloud Gate sculpture, affectionately known as The Bean . The park is a perfect setting for leisurely strolls or picnics amidst the city skyline.
- Willis Tower: Ascend to new heights at Willis Tower, one of the tallest skyscrapers in the United States. The Skydeck offers breathtaking panoramic views of the city and beyond, providing an exhilarating experience that showcases Chicago's impressive architecture.
- Art Institute of Chicago: Immerse yourself in culture at the Art Institute of Chicago, home to an extensive collection of artworks spanning centuries. From Impressionist masterpieces to contemporary art, this renowned museum offers a deep dive into artistic heritage and creativity.
Best time to go to Downtown Chicago
The best time to visit Downtown 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.
Tips to save on your trip to Downtown Chicago
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Downtown Chicago.
- 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 Downtown Chicago holiday package cost?
Go from looking to booking with our Downtown Chicago holiday packages, which start from just . Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.
How do I get a cheap travel package to Downtown Chicago?
Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago holiday package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The holiday you've always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago holiday?
While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.
What does an Expedia Downtown Chicago travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Downtown Chicago travel package?
Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Downtown Chicago Expedia holiday package?
Yes — that's the beauty of an Expedia holiday package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.
If I'm not able to travel, can I cancel my Downtown Chicago holiday package?
You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago holiday package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.