Downtown Chicago 2024 Holidays

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Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
9 Jul - 13 Jul
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Amazing. Definitely coming back!

Reviewed on 20 Apr 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
9 Jul - 13 Jul
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,012 reviews)
Great place to stay. My new Chicago hotel

Reviewed on 27 Apr 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
9 Jul - 13 Jul
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
9 Jul - 13 Jul
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (650 reviews)
Great customer service

Reviewed on 21 Apr 2024

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
9 Jul - 13 Jul
Return direct flight included
Dublin (DUB) to Chicago (ORD)
7.8/10 Good! (1,007 reviews)
The front staff stated they had no access to laundry. I was needing an extra blanket and did not receive.

Reviewed on 22 Apr 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

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

Find hotels in Magnificent Mile

Top hotels in Downtown Chicago

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €115 per night from 30 Apr to 1 May
€115
per night
30 Apr - 1 May
7.6/10 Good! (2,534 reviews)
"My stay was very wonderful and pleasant"

Reviewed on 27 Apr 2024

Warwick Allerton - 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 €124 per night from 29 Apr to 30 Apr
€124
per night
29 Apr - 30 Apr
7.6/10 Good! (6,589 reviews)
"This hotel sometimes gets a bad rap for being old and for some things being outdated. But my room this time has been completely remodeled and was quite nice. They even replaced the 100yr old toilet flushing fixture and the bathroom was completely updated. The price was merely double the hostel. Hopefully ..."

Reviewed on 25 Apr 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €155 per night from 29 Apr to 30 Apr
€155
per night
29 Apr - 30 Apr
8.6/10 Excellent! (2,822 reviews)
"Small room is my only complaint, seems they cut the room in half, other that that room was quite and dining options around hotel were good"

Reviewed on 27 Apr 2024

River Hotel
See all 1,612 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.

Frequently asked questions

How much does a Downtown Chicago holiday package cost?
Go from looking to booking with our Downtown Chicago holiday packages, which start from just €1,073. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.
How do I get a cheap travel package to Downtown Chicago?
Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago holiday package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It’s an easy way to unlock even more savings. The holiday you’ve always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago holiday?
While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you’ll score some incredible deals. If you’ve left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.
What does an Expedia Downtown Chicago travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you’ve made your booking. You’re in charge! When you combine your bookings with Expedia, you’ll score discounts you won’t find elsewhere.
What should I know before booking a Downtown Chicago travel package?
Our prices are always low. However, you’ll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll get transparent pricing and tons of choice.
Can I choose my airline with a Downtown Chicago Expedia holiday package?
Yes — that’s the beauty of an Expedia holiday package. You’re in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.
If I'm not able to travel, can I cancel my Downtown Chicago holiday package?
You can. We understand that even the best-laid plans can go awry, so we’re happy to help if you have to make changes to your Downtown Chicago holiday package. You may be able to change or cancel your itinerary for free if you’ve booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

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 Chicago Pizza Tour

Chicago Pizza Tour

€69
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

€20
Per adult
90% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

€43
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
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.