Downtown Chicago Holidays from £1,267

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to £195 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Packages with flights are ATOL protected

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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
8 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (703 reviews)
The location of the hotel was very convenient to shopping, parks, restaurants, museums, etc. The bed was really comfortable. The bathroom was nice, but the lighting was really dim. The lighting in the hallways on our floor was really dim as well. There were coffee and apples available in the lobby in the morning, but no bananas as indicated on the sign. Also, the coffee was gone one morning by 9:30 am. It seems like coffee should at least be available to guests most of the day for the price of the rooms. We were also disappointed that the rooftop bar was closed, even though it indicated online that it would be open over Memorial Day weekend.

Reviewed on 6 Jun 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
8 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Property is 5 star all the way. Staff is excellent. Restaurant is 5 star as well.

Reviewed on 6 Jun 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
8 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (208 reviews)
The staff here is amazing and so helpful. Loved my stay here.

Reviewed on 6 Jun 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
8 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
Easy access to all attractions if not all walkable to shopping restaurants and excellent service on the concierge

Reviewed on 7 Jun 2024

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
per person
8 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
Well kept, great location and friendly staff!

Reviewed on 31 May 2024

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 £137 per night from 17 Jun to 18 Jun
£137
per night
17 Jun - 18 Jun
7.6/10 Good! (6,869 reviews)
"Very classy historic hotel. Comfortable beds, clean rooms."

Reviewed on 8 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
Fully refundableReserve now, pay when you stay
The price is £186 per night from 16 Jun to 17 Jun
£186
per night
16 Jun - 17 Jun
8/10 Very Good! (2,364 reviews)
"I loved everything about this property. It was easy to take public transportation with nearby buses and trains.It was close to everywhere i wanted to be and see. Food was good, everything was spotless and smelled really good in the lobby and the suite. I was very comfortable and will definitely stay ..."

Reviewed on 5 Jun 2024

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £157 per night from 30 Jun to 1 Jul
£157
per night
30 Jun - 1 Jul
8.6/10 Excellent! (2,952 reviews)
"Excellent stay for us. The room was clean and comfortable. The staff was exceptional. Very professional and friendly. Couldn't ask for a better experience. Thanks."

Reviewed on 5 Jun 2024

River Hotel
See all 1,677 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

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 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
Image for Millennium Park

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

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

£59
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

More trip options

* 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.