Chicago Holidays

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    Better together
    Save up to €185 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Chicago

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
27 Dec - 1 Jan
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
The staff were all wonderful and really helpful. It was our first time in Chicago and they were more than wonderful for pointing us in the correct locations on where we needed to go and what to do

Reviewed on 5 Nov 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
27 Dec - 1 Jan
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Service was great, room was neat and very clean. Would stay again!

Reviewed on 4 Oct 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
27 Dec - 1 Jan
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
The hotel was beautiful, fabulous location , my only concern that I’m only giving 4 and not 5 is because we were not greeted on arrival, nothing was explained, boarding on rudeness. Bell man great

Reviewed on 9 Nov 2024

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
per person
27 Dec - 1 Jan
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The best place to stay in Chicago!

Reviewed on 10 Nov 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
27 Dec - 1 Jan
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Top notch hotel in a great location. Home away from home feel. Stellar customer service. Restaurant onsite with a great bar and stunning views. For discerning travelers this is about as good as it gets in Chicago.

Reviewed on 10 Nov 2024

Where to stay in Chicago

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

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in 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 €94 per night from 24 Nov to 25 Nov
€94
includes taxes & fees
24 Nov - 25 Nov
7.8/10 Good! (8,061 reviews)
"A bit dated and our room did not look like any of the photos but it was charming in a quirky way and everyone was very nice and helpful. Location was great."

Reviewed on 10 Nov 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 €119 per night from 8 Dec to 9 Dec
€119
includes taxes & fees
8 Dec - 9 Dec
8.6/10 Excellent! (3,531 reviews)
"The view is nice, but the property isn’t worth the price I paid for it"

Reviewed on 9 Nov 2024

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 €129 per night from 24 Nov to 25 Nov
€129
includes taxes & fees
24 Nov - 25 Nov
8.2/10 Very Good! (3,184 reviews)
"Very clean!"

Reviewed on 10 Nov 2024

Embassy Suites by Hilton Chicago Downtown River North
See all 4,829 properties in 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 Chicago holiday package cost?
Starting from as low as €2,195, you can handcraft your own Chicago package the way you want. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Chicago?
Find flights that fit in with your schedule, add a hotel to your booking and watch how much you save with a Chicago holiday package. It’s as easy as that! From flights and hotels to activities and rental cars, Expedia is where your cheap getaway begins. And with more than 550 partner airlines and 1,000,000 properties across the globe to pick from, you won’t be short of choice.
Where should I stay in Chicago?
Central Chicago is an excellent place to stay in Chicago. With interesting attractions like Millennium Park and Willis Tower within easy reach, you won’t have to worry about running out of things to do here. Magnificent Mile is another option. This place has plenty to offer travellers, including John Hancock Centre and Chicago Water Tower.
What are the top hotels in Chicago?
Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are some favourite options in the neighbourhood of Central Chicago. If you’d rather stay in the North Side area, consider locking in a room at The Whitehall Hotel or Hyatt Regency Chicago.
How far in advance should I book my Chicago holiday?
While not all air carriers release ticket prices early, you can normally start comparing international flights on Expedia up to 12 months in advance. This is the time you can bag some fantastic deals. If you’re booking last minute, you may still be in luck. Discounted prices occasionally appear a few weeks prior to departure.
What does an Expedia Chicago travel package include?
Hotels, flights and rental cars — we have them well covered. With Expedia, you can shape your Chicago package just how you like it. All you have to do is work out exactly what you need. Once you’ve made your booking, you can add on fun things like tours and activities. The more you bundle, the greater your savings!
What should I know before booking a Chicago travel package?
We already have low prices. However, you’ll pick up even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and a huge range of choice.
Can I choose my airline with a Chicago Expedia holiday package?
Yes, of course. We have more than 550 partner airlines globally, so fly with the carrier that fits your budget and travel needs.
If I'm not able to travel, can I cancel my Chicago holiday package?
We totally get that life sometimes gets in the way of your plans. If you’ve booked a Chicago holiday package and have to amend or cancel it, we’re here to help. We suggest visiting our Customer Service Portal first for information. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change your itinerary at no cost. If it’s been longer than 24 hours, your airline, hotel or car rental company may charge a fee.

Popular places to visit

Image for Michigan Avenue

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
Image for 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
Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field

What to do in Chicago

Image for Flyover in Chicago

Flyover in Chicago

€35
Per adult
94% of travellers recommend
Flyover in Chicago
Image for Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

€41
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Image for Chicago River Cocktail Cruise

Chicago River Cocktail Cruise

€55
Per adult
90% of travellers recommend
Chicago River Cocktail 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.