Central Chicago Holidays

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Top Flight + Hotel Deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
14 Mar - 20 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8/10 Very Good! (1,394 reviews)
Nice, affordable property. Lots of restaurants in the area.

Reviewed on 6 Jan 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
14 Mar - 20 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,253 reviews)
Always friendly and clean hotel. Love the club access on the too floor.

Reviewed on 5 Jan 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
14 Mar - 20 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (279 reviews)
Besides hallways being loud and like frat house from 1 to 3am , the police showing up it was very great

Reviewed on 6 Jan 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
per person
13 Mar - 20 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
We liked how attentive thw staff was. My date had a tag still attatched to him that we missed while heading out for brunch and shopping and the gentleman at the desk waived him over and let him know. Paid attention to the guest. We will definitely be back. Great staff

Reviewed on 6 Jan 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
14 Mar - 20 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,469 reviews)
The view for the fireworks was amazing! I didn't like the fact that my wife and I both woke up with some kind of bug bites on our lower legs and on top of our feet!

Reviewed on 7 Jan 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

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 Central 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 €105 per night from 11 Jan to 12 Jan
€105
includes taxes & fees
11 Jan - 12 Jan
7.8/10 Good! (8,376 reviews)
"Beautiful area, although not many great food options around. The hotel is pretty outdated, but charming. Also, constant sirens in and around the area…. don’t know how the locals handle it! Although, the transportation is amazingly connected but kinda sketch."

Reviewed on 6 Jan 2025

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 €109 per night from 16 Jan to 17 Jan
€109
includes taxes & fees
16 Jan - 17 Jan
8.6/10 Excellent! (3,689 reviews)
"Downtown"

Reviewed on 6 Jan 2025

River 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 €111 per night from 15 Jan to 16 Jan
€111
includes taxes & fees
15 Jan - 16 Jan
8.2/10 Very Good! (3,452 reviews)
Weekend Getaway
"Checkin was quick and smooth Room was clean and nice. Plenty of amenities and restaurants and bars in the area."

Reviewed on 5 Jan 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 1,491 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.

Frequently asked questions

How much does a Central Chicago holiday package cost?
Go from wondering to wandering with our Central Chicago holiday packages, which start from just €1,205. Pick the flights and hotels that match your travel plans. Then, add on some activities or tours for a one-of-a-kind escape.
How do I get a cheap travel package to Central Chicago?
Browse and lock in everything in one place with our Central Chicago holiday packages. You’ll discover bargains on hotels, flights and more that’ll keep your travel budget happy and your adventurous spirit full. And, with more than 550 air carriers and 1,000,000 hotels around the globe to choose from, you’ll have endless opportunities to mix and match your own way.
Where should I stay in Central Chicago?
A journey to Central Chicago isn’t complete without stopping by Wrigley Field and McCormick Place. Stay at a hotel nearby so you can easily access these terrific sights.
What are the top hotels in Central Chicago?
Hilton Garden Inn Chicago Central Loop and Kasa River North Chicago are among the most sought-after properties in Central Chicago. Why not have a look at the rates and facilities at each and then make a decision?
How far in advance should I book my Central Chicago holiday?
Search Expedia to compare international flights as early as possible. You can generally purchase a seat up to a year before departure. If you don’t see your preferred carrier, or you’ve left things to the last moment, don’t worry. Cheap fares to Central Chicago sometimes emerge a few weeks before the date of departure.
What does an Expedia Central Chicago travel package include?
Flights, car rentals and hotels — we connect you to the very best deals. All you’ll have to do is pick your favourite combination. Once you’ve made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an exciting Central Chicago trip.
What should I know before booking a Central Chicago travel package?
You can save big by bundling your hotels, flights and rental cars. Once you’ve made your booking, you can add on tours and activities. Your next unforgettable holiday is only a couple of clicks away.
Can I choose my airline with a Central Chicago Expedia holiday package?
With a holiday package, the choice is in your hands. Whether you’d like to fly to Central Chicago in coach or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Central Chicago holiday package?
Because we understand life can be unpredictable, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.

Popular places to visit

Magnificent Mile - River North showing 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
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
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

What to do in Central Chicago

Flyover in Chicago

Flyover in Chicago

€36
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

€47
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

€33
per adult
Color Factory Chicago Ticket
See all activities in Central Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.