Downtown Chicago Holidays
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The Latest Downtown Chicago Holiday Packages
- The Talbott, Autograph Collection
30 Dec - 1 JanThe Talbott, Autograph Collection + Flight
Downtown Chicago2 nights4.5 star property9.4/10 - Exceptional (194 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,291€1,188found 1 day agoper traveller - Hotel Saint Clair- Magnificent Mile
30 Dec - 1 JanHotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago2 nights4.0 star property8.6/10 - Excellent (2,379 reviews)"The room was extremely cold. Heater worked fine, but there was a leak in the sealant on the window, so throughout the night very cold air was coming in. Other than that it was fine for a one night stay"Reviewed November 7, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,374€1,241found 1 day agoper traveller - Hotel 505 River North
30 Dec - 1 JanHotel 505 River North + Flight
Downtown Chicago2 nights4.5 star property9.2/10 - Wonderful (3,006 reviews)"Deben actualizar las TVs"Reviewed November 7, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,423€1,317found 1 day agoper traveller - Kinzie Hotel
30 Dec - 1 JanKinzie Hotel + Flight
Downtown Chicago2 nights4.0 star property9.2/10 - Wonderful (2,174 reviews)"Overall, a decent property and convenient location for visiting Chicago for business travel. The rooms could be spruced up a bit. The bathroom is outdated. Elevators could also use a refresh."Reviewed November 6, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,328€1,237found 1 day agoper traveller - Hotel Chicago Downtown, Autograph Collection by Marriott
30 Dec - 1 JanHotel Chicago Downtown, Autograph Collection by Marriott + Flight
Downtown Chicago2 nights4.0 star property9.2/10 - Wonderful (1,002 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,310€1,225found 1 day agoper traveller
Where to stay in Downtown Chicago
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
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
Architecture River Tour from Michigan Avenue
Downtown Chicago Hotel Deals
"The main area of the hotel is old and beautiful. The rooms are quite basic and due for upgrades. The bathroom had stool on the toilet when we arrived. No fan in the bathroom or working window so the room got very humid when we showered. I’m surprised that I didn’t see mold. Bed was comfy."
"Deben actualizar las TVs"
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
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 🎇"
Cambria Hotel Chicago Loop - Theatre District
Cambria Hotel Chicago Loop - Theatre District"It was a nice quiet space and very clean. The rooms is nice and I would revisit again."
"Un hotel con vista espectacular. Personal súper calificado. Ubicado en la mejor zona y muy accesible para poder llegar caminando a donde quieras."
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileFind out more about Downtown Chicago
Things to do in and around Downtown Chicago
Downtown Chicago offers a delightful blend of family-friendly and outdoor activities, making it ideal for city-themed holidays. Visitors can indulge in shopping at various boutiques, enjoy thrilling events at arena entertainment facilities, and catch a show at the local theatres. Don't miss the chance to explore the Holiday Inn, a notable spot for accommodations and dining, enhancing your stay in this vibrant urban setting.
Shopping
In Downtown Chicago, visit Chicago Place Mall for a vibrant shopping experience, offering a mix of city and family vibes. The 900 North Michigan Shops combines business and entertainment, perfect for all. Don't miss the Maxwell Street Market, a lively spot with a unique array of local goods.
Recreation
Experience the vibrant atmosphere at the United Center, where you can catch a thrilling sporting event. For a touch of culture, the Apollo Theater Chicago offers a romantic and entertaining setting perfect for families. Don't miss Lincoln Hall for an unforgettable night of live music in an engaging environment.
Adventure
Experience the thrills at Amazing Chicago's Funhouse Maze, where family adventure awaits. Take a ride on the Centennial Wheel for breathtaking views of the skyline. For a taste of nature, explore the scenic Salt Creek Trail, a hiking path located 19.3km from the heart of Downtown Chicago.
Nightlife
Downtown Chicago buzzes with vibrant nightlife. Visit Dave & Buster's for a lively pub atmosphere, then head to Kingston Mines or Blues on Halstead for an electric nightclub experience, both offering fantastic entertainment and a romantic city vibe just a few miles away.
Find the best attractions in Downtown Chicago
Downtown Chicago offers a delightful blend of family-friendly activities, outdoor spaces, and urban charm, making it an ideal destination for various types of vacations. Visitors can explore iconic skyscrapers, scenic urban parks, and vibrant streets. Cultural experiences abound, with attractions such as the Chicago River and numerous museums. Whether you're seeking top sights or engaging family experiences, Downtown Chicago has something for everyone to enjoy.
- Michigan Avenue: Experience the vibrant heart of Downtown Chicago along Michigan Avenue, known for its upscale shopping, dining, and iconic architecture. Stroll past historic buildings and modern skyscrapers, soaking in the bustling city atmosphere.
- Navy Pier: Discover the charm of Navy Pier, a lively jetty offering stunning views of Lake Michigan. Enjoy various attractions, from amusement rides to cultural events, while mingling with friendly locals in a picturesque setting.
- Millennium Park: Relax in Millennium Park, an urban oasis perfect for families and outdoor enthusiasts. Admire the famous Cloud Gate sculpture, enjoy concerts, and participate in seasonal activities against the stunning city backdrop.
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
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Downtown Chicago.
- 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 €1,188. 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.