Chicago Holidays

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Your Chicago Holiday

Choose a Chicago holiday package and focus on what matters — having some fun. There's no more travel planning headaches, just lots more time to uncover the best of this interesting city, such as its cosmopolitan vibe and cultural experiences. Wrigley Field, Millennium Park and Willis Tower are just a few of the many attractions worth checking out during your trip to Chicago. Whoever you're taking a break with and whatever your budget, your dream Chicago holiday is just a few clicks away with Expedia.

Our guide on where to stay in Chicago

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

Chicago Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
2,720,500
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Chicago Riverwalk, Shedd Aquarium and Art Institute of Chicago

Our pick of the best Chicago Hotel Deals

Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 24 Mar to 25 Mar
AU$168
per night
24 Mar - 25 Mar
8.4/10 Very Good! (2,874 reviews)
"My whole experience with this hotel was fantastic. All of the staff were friendly and accommodating. Lovely rooms , quiet and great ammenities. Loved the Nespresso machine and hand/body lotion . Danny at check out was one of the friendliest people I’ve meet at any hotel I’ve stayed at . Was interested ..."

Reviewed on 17 Mar. 2024

Club Quarters Hotel, Central Loop, 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 AU$192 per night from 1 Apr to 2 Apr
AU$192
per night
1 Apr - 2 Apr
7.6/10 Good! (6,339 reviews)
"Nice location. Historic building with charm, but not shiny and new. Bed was extremely comfortable but my room faced the L so it was rather noisy. Maintenance being done on elevators on a busy friday night was inconvenient."

Reviewed on 16 Mar. 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 AU$185 per night from 31 Mar to 1 Apr
AU$185
per night
31 Mar - 1 Apr
8.6/10 Excellent! (2,655 reviews)
"Love it"

Reviewed on 17 Mar. 2024

River Hotel
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.

Explore other types of vacation packages

Frequently asked questions

How much does a Chicago holiday package cost?
Starting from as low as , 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.

Discover the most popular places to visit in Chicago

What to do in Chicago

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