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Holidays in Chicago

Choose two or more items and save on your trip:

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

    The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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    Magnificent Mile - River North

    Magnificent Mile

    An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

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    The Loop - Downtown which includes a river or creek

    The Loop

    3 out of top 10 points of interest in this area

    4.5/5Wonderful!(93 area reviews)

    Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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    Chicago showing a city and modern architecture

    Lincoln Park

    5/5Exceptional!(4 area reviews)

    Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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    Gold Coast which includes street scenes as well as a couple

    Gold Coast

    Enjoy upscale shopping, varied dining experiences and waterfront walks at this affluent suburb set on the shores of Lake Michigan.

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Top hotels in Chicago

Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3 out of 5
243 E. Ontario, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is NZ$184 per night from 18 Apr. to 19 Apr.
4.4/5Excellent! (1,371 reviews)

"Convenience to downtown"…"

Reviewed on 9 Apr. 2021

Aloft Chicago Mag Mile
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 NZ$282 per night from 12 Apr. to 13 Apr.
4.6/5Wonderful! (2,691 reviews)

"The People at the main entrance are great....."…"

Reviewed on 9 Apr. 2021

LondonHouse Chicago, Curio Collection by Hilton
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is NZ$249 per night from 12 Apr. to 13 Apr.
4.3/5Excellent! (1,859 reviews)

"Everything has to buy Even WiFi is common and free in smallest hotels But swiss hotel charges for that too That was a bit disappointing"…"

Reviewed on 10 Apr. 2021

Swissotel - Chicago
See all 2610 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.

Top activities in Chicago

Image for 360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck (Hancock Center)

NZ$35
Per adult
86% of travellers recommend
360 CHICAGO Observation Deck (Hancock Center)
Image for Chicago Mob Tour: Criminals & Gangsters Bus Tour

Chicago Mob Tour: Criminals & Gangsters Bus Tour

NZ$62
Per adult
90% of travellers recommend
Chicago Mob Tour: Criminals & Gangsters Bus Tour
Image for Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS: Admission to Top 5 Chicago Attractions

NZ$151
Per adult
94% of travellers recommend
Chicago CityPASS: Admission to Top 5 Chicago Attractions
See all 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 January, while October is when hotel rates generally rise. Chicago draws the crowds in July, June, May. If you want a more relaxed escape, October, December, November 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.

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