Central Chicago Holidays from £1,057

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The Latest Central Chicago Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Little disappointed there was no free breakfast

Reviewed on 1 May 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (650 reviews)
It's really a beautiful looking Hotel and the rooms are very nice and clean. they play loud obnoxious music in the Lobby which I guess a teenager would probably like. Read the fine print. they have a $41 a day "Destination fee" which gets you a cup of coffee from 6am-9am(Not great coffee and not always hot) and bottles of water. A welcome drink (only first day) if you use their mix which they add a shot)They say there is a shuttle service (first come first serve) they don't tell you that it is only on the weekend until you ask about it Monday Morning. $41 dollars a day for that? This needs to be addressed. I feel it is an excuse to get more money out of you. I stayed three nights and was hit for $123. My fault I didn't see the charge that was down at the end of the page. A lot of street noise but Hotel was quiet by itself and the Maids were so friendly and sweet.

Reviewed on 30 Apr 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (3,485 reviews)
The view from the London House down the river was fantastic. Great staff, great location.

Reviewed on 1 May 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on 10 Jan 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,012 reviews)
Nice property,excellent location

Reviewed on 30 Apr 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Good location, nice vibe, amazing staff!

Reviewed on 30 Apr 2024

Central Chicago Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Our guide on where to stay in Central Chicago

Check out a few of the areas and neighbourhoods we love in Central Chicago Learn more about Central Chicago
Downtown Chicago featuring a city

Downtown Chicago

8 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Our pick of the best Central Chicago Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (6,629 reviews)
"I like the Congress Plaza because it's still a reasonably priced downtown hotel that is close to a lot of downtown attractions. I didn't find the counter staff particularly professional, friendly, or helpful this particular visit. Was a bit disappointed by that. Otherwise, we liked our rooms (539 ..."

Reviewed on 1 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service and a fitness centre. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,834 reviews)
"Loved the free water. Hotel staff (Pedro) was very friendly & helpful! The room was the perfect size for one person."

Reviewed on 30 Apr 2024

River Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this family-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness centre and valet parking. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (2,542 reviews)
"Its was a nice stay."

Reviewed on 30 Apr 2024

Warwick Allerton - Chicago
See all 1,453 properties in Central Chicago
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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 £1,057. 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.

Discover the most popular places to visit in Central Chicago

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(36 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.

McCormick Place
Image for Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Unmissable things to do in Central Chicago

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

£43
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

£59
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago Museum of Contemporary Art: General Admission Ticket

Chicago Museum of Contemporary Art: General Admission Ticket

£17
Per adult
90% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
See all activities in Central Chicago

* 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.