Central Chicago Holidays from £1,017
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Top Central Chicago Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
£1,111
per person
3 Nov - 10 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on 26 Aug 2026
Swissotel - Chicago
Downtown Chicago
£1,152
per person
3 Nov - 10 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on 26 Aug 2026
Where to stay in Central Chicago
Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Central Chicago
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
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.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
Streeterville
Navy Pier and Michigan Avenue are just a few worthwhile attractions to visit in Streeterville. Travellers also love the fascinating museums, panoramic lake views and popular shops.
Near North Side
Known for its fascinating museums, panoramic lake views and popular shops, there's plenty to explore in Near North Side. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at Clark-Division Station or Chicago Station (Brown Line) to see more of the city.
Central Chicago Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Top hotels in Central Chicago
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£91
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£117
31 Aug - 1 Sept
includes taxes & fees
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.
Stay near popular Central Chicago attractions
Navy Pier
9.0/10 (24,140 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Photo by © Cesar Russ Photography
McCormick Place
8.8/10 (9,822 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Chicago Riverwalk
9.6/10 (13,574 reviews)
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
Millennium Park
9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Michigan Avenue
9.4/10 (15,813 reviews)
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Grant Park
9.2/10 (12,844 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Art Institute of Chicago
9.4/10 (7,898 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
What to do in Central Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
Frequently asked questions
How much does a Central Chicago travel package cost?
Be ready to book, because a trip to Central Chicago starts from an affordable £1,017. When you combine your flights, hotels and car rentals into a travel package, you'll pick up the best bargains.
If I'm not able to travel, can I cancel my Central Chicago travel package?
It's difficult to predict what the future holds, so it's good to know that you can cancel or change your Central Chicago travel package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Central Chicago?
Booking a flight and hotel together with Expedia won't just save valuable time — it'll save you a nice amount too. A Central Chicago travel package makes it a cinch to put together your dream adventure. With more than 550 airlines throughout the world to choose from, finding convenient flights that fit your busy schedule won't be a problem. On top of that, we have over 1,000,000 properties globally to select from. Talk about choice! No matter who you are, Expedia puts more of the world within your reach.
Does Expedia offer Book Now, Pay Later Central Chicago holidays?
Expedia has joined forces with online lender Klarna to make your next getaway easier on your budget. Paying in instalments means you can spread the costs of your next big adventure, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Take a look at these flexible payment options:
- Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's monthly instalment plans. If paying small amounts each month sounds right for you, pick this option during the checkout process.
- Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
- Low deposit holidays: Clicking on the "book now" button is easier with this payment option. Simply put down a small deposit on your escape and then start packing your suitcase.
Where should I stay in Central Chicago?
Most who travel to Central Chicago include both Millennium Park and Wrigley Field on their bucket lists. Why not reserve a hotel near these top attractions?
What are the top hotels in Central Chicago?
Reserve a room at Hyatt Regency Chicago. It's one of this area's most in-demand hotels. Another top option in Central Chicago is The Godfrey Hotel Chicago.
How far in advance should I book my Central Chicago holiday?
It's always wise to book early. Airlines typically release flights up to a year prior to departure, and this is a perfect opportunity to pick up some of the lowest prices. Just been told you need to take some holiday time next week? No problem! Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Central Chicago travel package include?
Hotels, rental cars and flights, or any combination of the three — the choice is all yours! Whether you're exploring Central Chicago with the whole family or enjoying a solo break, there's a package to match your budget and style. Once you've made your booking, why not add on some tours or activities?
What should I know before booking a Central Chicago travel package?
Whether it's relaxation or adventure you're after, a Central Chicago travel package lets you organise your escape your way. Plus, you'll get access to great discounts when you combine your hotel with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Central Chicago Expedia travel package?
Yes, you're in charge. We have access to over 550 partner airlines across the globe, so you can customize your Central Chicago escape according to your travel preferences.
Explore a world of travel with Expedia
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- Flights to Chicago
- American Airlines Dublin (DUB) to Chicago (ORD) flights
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- Art Institute of Chicago
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- Michigan Avenue
- Millennium Park
- Montrose Beach
- Navy Pier
- Northwestern University
- Robie House
- Shops at North Bridge
- The Loop Holidays
- Unity Temple
- Willis Tower
- Wrigley Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
