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Chicago, IL Vacation Packages

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 which includes a river or creek

    The Loop

    3 out of top 10 points of interest in this area

    4.5/5Wonderful!(9,480 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
    Shops at North Bridge showing a city, central business district and street scenes

    River North

    Known for its fantastic nightlife, stunning river views, and popular shops, there's plenty to explore in River North. Top attractions like House of Blues Chicago and Chicago Riverwalk are major draws. Catch the metro at Chicago Station (Brown Line) or Merchandise Mart Station to see more of the city.

    Find hotel + flight trips in River North
    Chicago which includes modern architecture and a city

    Lincoln Park

    4.5/5Wonderful!(320 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

Top Hotels in Chicago

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is NT$2,779 per night from Apr 19 to Apr 20
4.2/5Excellent! (2,375 reviews)
"Awesome Hotel, they have great service and very very clean, definitely is worth the every penny, recommend staying here it is a great location!"

Reviewed on 2021/4/17

River Hotel
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 NT$4,788 per night from Apr 28 to Apr 29
4.6/5Wonderful! (2,697 reviews)
"Modern rooms, albeit small. Friendly and responsive staff."

Reviewed on 2021/4/16

LondonHouse Chicago, Curio Collection by Hilton
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is NT$4,552 per night from Apr 19 to Apr 20
4.4/5Excellent! (3,286 reviews)
"Staff was very friendly and hotel was very nice. Would be nice to have complimentary water in your room though."

Reviewed on 2021/4/13

Hyatt Regency Chicago
See all 2596 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 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 42%, as a matter of fact! A Chicago vacation package makes it simple to put together the ideal trip. With more than 500+ 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 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 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 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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