Downtown Chicago Holidays

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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €957, price is now €797 per person
€797
per person
28 Apr - 30 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everyone are helpful breakfast is amazing

Reviewed on 20 Feb 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,061, price is now €937 per person
€937
per person
28 Apr - 30 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on 31 Jan 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,041, price is now €928 per person
€928
per person
28 Apr - 30 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Nice hotel Great location

Reviewed on 15 Feb 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €937, price is now €845 per person
€845
per person
28 Apr - 30 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Everything was amazing

Reviewed on 17 Feb 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was €875, price is now €806 per person
€806
per person
28 Apr - 30 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (2,972 reviews)
Clean and spacious rooms. Great location!

Reviewed on 16 Feb 2026

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 €189 per night from 13 Mar to 14 Mar
€189
13 Mar - 14 Mar
includes taxes & fees
8/10 Very Good! (9,913 reviews)
Everything was clean and neat.

Reviewed on 19 Feb 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €123 per night from 4 Mar to 5 Mar
€123
4 Mar - 5 Mar
includes taxes & fees
9.4/10 Exceptional! (3,377 reviews)
Everyone are helpful breakfast is amazing

Reviewed on 20 Feb 2026

Hotel Riu Plaza Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €163 per night from 27 Feb to 28 Feb
€163
27 Feb - 28 Feb
includes taxes & fees
8.4/10 Very Good! (2,643 reviews)
Great room, friendly staff.

Reviewed on 19 Feb 2026

Hilton Chicago
See all 1,679 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 €797. 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

Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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 featuring a sunset and rides

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 featuring street scenes, autumn leaves and modern architecture

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€22
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€33
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€20
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.