Central Chicago Holidays from £612

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Top Central Chicago Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was £972, price is now £612 per person
£612
per person
8 Nov - 13 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,400, price is now £838 per person
£838
per person
8 Nov - 13 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,738, price is now £1,078 per person
£1,078
per person
8 Nov - 13 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,303, price is now £1,465 per person
£1,465
per person
8 Oct - 15 Oct
found 3 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Loved the view from the room of Lake Michigan.

Reviewed on 25 Aug 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,683, price is now £1,074 per person
£1,074
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
We loved the experience! We shall come back again😊

Reviewed on 24 Aug 2025

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 - 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

Central Chicago Essential Information

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

Top hotels in Central Chicago

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
The price is £131 per night from 1 Sept to 2 Sept
£131
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,219 reviews)
"Friendly"

Reviewed on 24 Aug 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is £163 per night from 14 Sept to 15 Sept
£163
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,995 reviews)
"Transportation by bus or subway is within a 5 minute walk, very easy. Hotel is across from a beautiful park. Lobby is nice but the hallways look very rough. It’s an old hotel with basic upgrades. Rooms were clean but shows it age. Beds were comfy. We checked our luggage upon arrival because our room ..."

Reviewed on 23 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
The price is £169 per night from 2 Sept to 3 Sept
£169
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,886 reviews)
"Customer service amazing"

Reviewed on 24 Aug 2025

Palmer House a Hilton Hotel
See all 1,595 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

Popular places to visit

Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

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.

Michigan Avenue
Navy Pier

Navy Pier

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

Navy Pier
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

What to do in Central Chicago

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Central Chicago

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 £612. 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.

* 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.