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Holidays in Chicago

Choose two or more items and save on your trip:

Chicago Vacation: Coronavirus Information

Most Chicago hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Chicago trip, please visit our Coronavirus Information page.

Where to stay in Chicago

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

Top hotels in Chicago

The Godfrey Hotel Chicago
The Godfrey Hotel Chicago
4.5 out of 5
127 West Huron, at LaSalle, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is AU$113 per night from 6 Dec. to 7 Dec.
4.3/5Excellent! (1,586 reviews)

"Love everything! The hotel was nice and staff was generous."…"

Reviewed on 24 Nov. 2020

The Godfrey Hotel Chicago
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5
85 East Wacker Drive, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is AU$183 per night from 14 Dec. to 15 Dec.
4.6/5Wonderful! (2,593 reviews)

"Great location. Walking distance to many Chicago sites! Beautiful river/city view from our room. Check-in and checkout were quick and can be contactless. The rooms are also very clean! Going to be staying here next time I’m in Chicago :)"…"

Reviewed on 24 Nov. 2020

LondonHouse Chicago, Curio Collection by Hilton
Eurostars Magnificent Mile, previously Dana Hotel
Eurostars Magnificent Mile, previously Dana Hotel
4 out of 5
660 North State Street, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is AU$165 per night from 3 Dec. to 4 Dec.
4.5/5Wonderful! (1,763 reviews)

"Great Hotel I would stay again any day. The room had a great view."…"

Reviewed on 29 Nov. 2020

Eurostars Magnificent Mile, previously Dana 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.

Top activities in Chicago

Frequently asked questions

How much does a Chicago holiday package cost?
Go from wondering to wandering with our Chicago holiday packages, which start from just . Handpick the flights and hotels that suit your style. Then, add on a few sightseeing tours for a memorable escape.
If I'm not able to travel, can I cancel my Chicago holiday package?
We totally understand — life sometimes gets in the way of your plans. If you’ve booked a Chicago holiday package and have to cancel or amend it, we can help. It’s always worth checking out our Customer Service Portal first for information. But generally speaking, if you’ve taken out your package in the last 24 hours, you may be able to change your itinerary for free. If it’s been more than 24 hours, your hotel, airline or car rental company may impose a fee.
How do I get a cheap travel package to Chicago?
Bundling your hotel and flight with Expedia won’t just save valuable time — it’ll save you cash too. As much as $200, as a matter of fact! A Chicago holiday package makes it simple to put together the ideal trip. With more than 400 airlines throughout the world to select from, finding flights that suit your schedule won’t be difficult. In addition to that, we’ve got over 1 000 000 hotel options globally to take your pick of. Now that’s what you call choice. Whatever your budget, Expedia puts more of the world within your reach.
Where should I stay in Chicago?
Downtown Chicago is a top contender for the best place to stay in Chicago. With interesting attractions like John Hancock Centre and Navy Pier nearby, you’ll never run out of things to do here. Near North Side is another popular choice. This neighbourhood has lots to see and do, such as Navy Pier and Chicago Childrens Museum.
What are the top hotels in Chicago?
Hyatt Regency Chicago and Congress Plaza Hotel are both well-liked options in the neighbourhood of Downtown Chicago. If you’re thinking of staying in the Near North Side area, consider booking a few nights at The Godfrey Hotel Chicago or Inn of Chicago.
When is the best time of year to visit Chicago?
You’ll have to consider your priorities to find the right answer. Typically, you’ll pick up the best deals in , while is when hotel rates generally rise. Chicago draws the crowds in . If you want a more relaxed escape, would be a better time to visit.
How far in advance should I book my Chicago holiday?
While prices change frequently, we generally suggest booking your holiday as early as possible. Many international airfares can be compared on Expedia up to 12 months in advance. If you’re booking last minute, you might still get lucky. Cheaper tickets to Chicago sometimes emerge in the weeks prior to departure.
What does an Expedia Chicago travel package include?
Packages include hotels, flights and rental cars, but you can combine any of them to create your perfect Chicago getaway. You can also add on fun stuff like tours and activities once you’ve made your booking. You’re in charge! When you bundle your bookings with Expedia, you’ll score discounts you won’t find anywhere else.
What should I know before booking a Chicago travel package?
You can save big by combining your flights, hotels and rental cars. Once you’ve made your booking, add on fun stuff like sightseeing tours or experiences. Your next unforgettable holiday is only a couple of clicks away.
Does Expedia offer Book Now, Pay Later Chicago holiday packages?
With one of our holiday packages, you can customize both your trip and a payment schedule. Expedia can help reduce financial burden to do with your travel with a Book Now, Pay Later booking, thanks to us working with online lender Affirm. That way, all you have to concentrate on is preparing to jet off into the sunset.
Can I choose my airline with a Chicago Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.