Downtown Chicago Holidays from £988

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Your Downtown Chicago Holiday

Reserving a Downtown Chicago holiday package is an ideal way to get to know this neighbourhood. From its well-known places to its little-known secrets, you won't be short of new adventures. Hoping to explore the sights during your trip to Downtown Chicago? Make sure you stop by nearby attractions like Millennium Park, Willis Tower and Art Institute of Chicago. Expedia will help put your travel plans into action. Book your dream Downtown Chicago holiday today.

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
per person
8 Sept - 12 Sept
found 17 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
I always recommend this hotel to my guests and book travel for other people here. Super friendly awesome staff, great place to stay downtown and very convenient location.

Reviewed on 30 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
7 Oct - 13 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The best location, everything within walking distance. The hotel is good, and the staff are friendly. Breakfast tasty. It meets all my expectations.

Reviewed on 30 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Sept - 12 Sept
found 18 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
7 Oct - 13 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (229 reviews)
We were pleasantly surprised and now already planned our next trip in a couple weeks to stay at the same hotel. Only concern is we were told pool area was open and hour after rooftop. That is mot correct and bed in single studio is too close to the wall. Had to crawl out as my wife sleep on the otherside. Other than that really like the stay.

Reviewed on 28 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 22 Sept
found 17 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown 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

Top hotels in Downtown Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £118 per night from 21 Aug to 22 Aug
£118
21 Aug - 22 Aug
includes taxes & fees
7.8/10 Good! (9,038 reviews)
"This was a nice option for my wife and I . Nice location plenty of dining with in walking distance. Highly recommend this hotel"

Reviewed on 29 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £225 per night from 17 Aug to 18 Aug
£225
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (2,129 reviews)
Overall a great family hotel
"Great time in Chicago and the hotel made it phenomenal! It’s in a very central location and allows access to all the major tourist attractions within walking distance. We really enjoyed Saturday movie night at the pool!"

Reviewed on 28 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £126 per night from 17 Aug to 18 Aug
£126
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,548 reviews)
"Great area, clean hotel but, parking is expensive. There was no pool."

Reviewed on 27 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,699 properties in Downtown 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

Why should I book my Downtown Chicago holiday with Expedia?
Expedia has your back for every detail of your next Downtown Chicago holiday. You'll always get the best deal possible, but when you bundle your flights, hotel and/or car hire into a holiday package, you'll save even more. Want to truly make the most of your escape? Add some awesome tours and activities to your package. We offer flexible cancellation policies on most bookings, so you won't need to worry if you have to change your plans. Head over to our Customer Service Portal link to find out more.
How do I get a cheap holiday to Downtown Chicago?
Secure flights that fit your busy schedule, add a hotel room to your booking and watch how much you save with a Downtown Chicago holiday. It's as simple as that! From hotels and flights to hire cars and tours, Expedia makes travelling cheaply a cinch. And with more than 400 air carriers and 321,000 hotel options globally to select from, you'll never be short of choice. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Downtown Chicago holiday?
There are plenty of things to put on your travel itinerary during your holiday in Downtown Chicago. Millennium Park, Willis Tower, Art Institute of Chicago and John Hancock Centre are a few of the major attractions.
Do I need a visa for my Downtown Chicago holiday?
Research the latest information on official government websites. Your nationality and whether you're visiting for study, leisure or business will determine if you need a visa for Downtown Chicago. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow sufficient processing time. Some visas may take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Downtown Chicago holiday?
Though everyone's style varies, it can help to have some guidelines for what to bring during your holiday in Downtown Chicago. Think about browsing style blogs before you head off for inspiration on local dress codes or fashion trends.
What does an Expedia Downtown Chicago holiday include?
Flights, hotels and hire cars — you'll find them all here. With Expedia, you can create your Downtown Chicago travel package however you want. All you have to do is decide exactly what you need. Once you've made your booking, why not add extras like activities and tours? The more you bundle, the greater the savings! Expedia has a wide selection of properties in Downtown Chicago, allowing you the freedom to personalise your holiday. Apartments and private holiday homes are two of the most sought-after stays for our customers here.
Does Expedia offer Book Now, Pay Later Downtown Chicago holidays?
We do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply pick the payment plan that works for you during checkout and take the stress out of budgeting for your next trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Browse our flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying in multiple transactions sounds right for you, choose this option at checkout.
  • No-deposit holidays: Pressing the "book now" button is easier with this payment plan. With no deposit required for your escape, you can Book Now, Pay Later and get on your way.

Can I choose my airline with a Downtown Chicago Expedia holiday?
Yes, and with more than 400 airlines to pick from globally, you're spoiled for choice. Have a look through the available options and see which airline suits your budget and needs.

Popular places to visit

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

Michigan Avenue

4.5/5(14 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.

Michigan Avenue
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
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

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

Millennium Park

Things to do

River tour boat in Chicago

Architecture River Tour

£36
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

£33
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
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in 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.