Central Chicago Holidays from £1,072

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The Latest Central Chicago Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
30 Aug - 4 Sep
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.8/10 Excellent! (216 reviews)
Very safe quiet property!

Reviewed on 17 Jun 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Aug - 14 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Staff was very friendly and helpful.

Reviewed on 15 Jun 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
8 Aug - 14 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,230 reviews)
Location is amazing, super friendly staff. Will definitely be back soon

Reviewed on 17 Jun 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Aug - 14 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Beautiful hotel with great service and amenities.

Reviewed on 17 Jun 2024

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Aug - 25 Aug
found 8 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,020 reviews)
Amazing staff and hard working housekeeping bomb service they surprise me with a special gift for the celebration of my 25 was very nice from start to finish rooms are always clean very spacious amazing high floor view beautiful bathroom . I Will always stay when I visit

Reviewed on 17 Jun 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
8 Aug - 14 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,114 reviews)
Amazing property in terms of location and amenities

Reviewed on 17 Jun 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
Magnificent Mile - River North

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

Find hotels in Magnificent Mile

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 Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (7,009 reviews)
"We were definitely surprised, and not in a good way about how small our room was. We had to shimy between the bed and air conditioner to get to the side of the bed, or crawl on the bed to get to that side."

Reviewed on 17 Jun 2024

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free breakfast, room service and a fitness centre. Our guests praise the breakfast and the helpful staff in their reviews. ...
8/10 Very Good! (2,405 reviews)
"It was ok had to keep asking for towels and the parking is to much look like they would give a discount for frequent visitors"

Reviewed on 18 Jun 2024

Embassy Suites by Hilton Chicago Downtown River North
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 Wi-Fi, room service and a fitness centre. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,954 reviews)
"This was such a conveniently located hotel. We were able to walk to so many places. The guy that checked us in was super friendly and set the tone for a really nice stay. I also really appreciated to cold filtered water stations all over to refill our water bottles. I would definitely stay here ..."

Reviewed on 16 Jun 2024

River Hotel
See all 1,474 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 £1,072. 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 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
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 Grant Park

Grant Park

4.5/5(96 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Unmissable things to do in Central Chicago

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

£149
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

£70
Per adult
100% of travellers recommend
Chicago Pizza Tour
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.