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Chicago Vacation Packages

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 showing 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.

    Find hotel + flight trips in Downtown Chicago
    Magnificent Mile - River North

    Magnificent Mile

    Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

    Find hotel + flight trips in Magnificent Mile
    The Loop - Downtown featuring a river or creek

    The Loop

    3 out of top 10 points of interest in this area

    4.5/5Wonderful!(725 area reviews)

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

    Find hotel + flight trips in The Loop
    Chicago which includes modern architecture and a city

    Lincoln Park

    5/5Exceptional!(20 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.

    Find hotel + flight trips in Lincoln Park
    South Loop which includes a high-rise building and a city

    South Loop

    2 out of top 10 points of interest in this area

    4/5Very Good!(31 area reviews)

    South of downtown Chicago, this neighborhood features cultural activities, sports and convention centers and a great dining and nightlife scene.

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Top Hotels in Chicago

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 CA $171 per night from Mar 7 to Mar 8
4.3/5Excellent! (1,831 reviews)

"The hotel was beautiful, I was a small bit upset with the response to service requests from the staff. I.E. I requested some fresh towels and that the dirty ones be picked up....that was never done. Otherwise, it was a great weekend trip...I suggest doing it for the cheap price of the great ..."…"

Reviewed on Mar. 1, 2021

Swissotel - Chicago
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown
3 out of 5
1 S Franklin Street, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is CA $90 per night from Mar 17 to Mar 18
4.4/5Wonderful! (2,007 reviews)

"Staff was friendly and the rooms were clean. Definitely worth what you pay."…"

Reviewed on Mar. 5, 2021

La Quinta Inn & Suites by Wyndham Chicago Downtown
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 CA $156 per night from Mar 10 to Mar 11
4.6/5Wonderful! (2,666 reviews)

"Hotel was absolutely beautiful! The beds are extremely comfortable and we had a really relaxing stay. My only complaint is that the elevators are really difficult. It took forever for us to get to our 10th floor room when everyone was heading up to the rooftop bar. Regardless, I would definitely ..."…"

Reviewed on Mar. 5, 2021

LondonHouse Chicago, Curio Collection by Hilton
See all 2455 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 things to do in Chicago

Image for 360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck (Hancock Center)

CA $32
Per adult
86% of travellers recommend
360 CHICAGO Observation Deck (Hancock Center)
Image for Go Chicago Explorer Pass: Choose 2,3,4 or 5 Top Attractions

Go Chicago Explorer Pass: Choose 2,3,4 or 5 Top Attractions

CA $85
Per adult
80% of travellers recommend
Go Chicago Explorer Pass: Choose 2,3,4 or 5 Top Attractions
Image for Chicago Mob Tour: Criminals & Gangsters Bus Tour

Chicago Mob Tour: Criminals & Gangsters Bus Tour

CA $58
Per adult
90% of travellers recommend
Chicago Mob Tour: Criminals & Gangsters Bus Tour
See all activities in Chicago

Frequently asked questions

How much does a Chicago vacation package cost?
Go from wondering to wandering with our Chicago vacation 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 vacation package?
We totally understand — life sometimes gets in the way of your plans. If you’ve booked a Chicago vacation 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 C$590, as a matter of fact! A Chicago vacation 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 321,000 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 Center and Navy Pier nearby, you’ll never run out of things to do here. Near North Side is another popular choice. This neighborhood 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 neighborhood 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 vacation?
While prices change frequently, we generally suggest booking your vacation 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 vacation is only a couple of clicks away.
Does Expedia offer Book Now, Pay Later Chicago vacation packages?
With one of our vacation 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 vacation 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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