How much does a Chicago vacation package cost?

Go from wondering to wandering with our Chicago vacation packages, which start from just $439. Handpick the flights and hotels that suit your style. Then, add on a few sightseeing tours for a memorable escape.

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.

Chicago, IL Vacation Packages | Travel Chicago 2021

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 (opens in new window).

Top Chicago Flight + Hotel Deals

The Langham, Chicago

River North

~~$930~~

$642

per person

Jul 23 - Jul 26

Roundtrip flight included

New York (NYC) to Chicago (CHI)

4.9/5Exceptional! (1,127 reviews)

Incredible location, amazing views, top-notch staff. We'll stay here again.

Reviewed on May 8, 2021

Residence Inn Chicago Downtown/Loop

Theatre District

~~$552~~

$439

per person

Jul 23 - Jul 26

Roundtrip flight included

New York (NYC) to Chicago (CHI)

4.7/5Exceptional! (968 reviews)

The actually had hot food service rather than the idiotic "new normal" of sack lunches. They actually had daily room service rather than the "new normal" of... well... not cleaning rooms daily as I've encountered this past year.

Reviewed on Apr 6, 2021

Swissotel - Chicago

Lakeshore East

~~$639~~

$516

per person

Jul 19 - Jul 23

Roundtrip flight included

Los Angeles (LAX) to Chicago (CHI)

4.2/5Very Good! (1,926 reviews)

The gym was fabulous! I would stay there again just for the gym alone. Front desk was quick and efficient. Super comfy beds and great location. Close enough to Michigan Ave without the crowd of people.

Reviewed on May 6, 2021

DoubleTree by Hilton Chicago Midway Airport

~~$664~~

$554

per person

Jul 20 - Jul 27

Roundtrip flight included

Los Angeles (LAX) to Chicago (MDW)

4.5/5Wonderful! (519 reviews)

Everything was great. There was a sticker on the outside of the door indicating that it was disinfected. The room did look clean. The building was nice. The only was when I went in the restroom to shower the pole on the side to help you in was dirty and there was a dirty towel over the top of the shower curtain, and the water took forever to go down the drain.

Reviewed on May 5, 2021

The Westin Chicago River North

River North

~~$598~~

$537

per person

Jul 23 - Jul 26

Roundtrip flight included

New York (NYC) to Chicago (CHI)

4.5/5Wonderful! (1,000 reviews)

Parking rates are outrageous. It wa $60 to park overnight

Reviewed on Mar 9, 2020

Where to stay in Chicago

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

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

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

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

75 East Wacker Drive, Chicago, IL

Free CancellationReserve now, pay when you stay

4.2/5Excellent! (2,365 reviews)

"Close to shopping, restaurants and movies"

Reviewed on May 8, 2021

The Whitehall Hotel

105 E Delaware Pl, Chicago, IL

Free CancellationReserve now, pay when you stay

4/5Very Good! (3,041 reviews)

"Perfect for a couple escape days n the Chicago city."

Reviewed on May 5, 2021

Loews Chicago Hotel

455 North Park Drive, Chicago, IL

Free CancellationReserve now, pay when you stay

4.7/5Exceptional! (1,369 reviews)

"Very beautiful and clean hotel, I highly recommend this hotel"

Reviewed on May 8, 2021

See all 2679 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

Chicago CityPASS: Admission to Top 5 Chicago Attractions

$109

Per adult

94% of travellers recommend

360 CHICAGO Observation Deck (Hancock Center)

$30

Per adult

84% of travellers recommend

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

$53

Per adult

80% of travellers recommend

See all activities in Chicago

What are the advantages of a road trip to Chicago?

There’s nothing quite like a Chicago road trip. And Expedia makes it easy for you to turn all those road trip ideas into reality. You can find cheap deals on hotels in Chicago or bundle your hotels with car rentals to save even more. With our Chicago packages, you’ll find hitting the highway for that road trip adventure is more affordable than ever.

How to plan a road trip to Chicago?

Planning a road trip can feel daunting, especially when you’ll be making multiple bookings for your itinerary. But you can find car rentals in Chicago and low rates on hotels all in one place— Expedia. How you plan your road trip depends on what’s important to you. People love to take road trips to experience the great outdoors, bond with friends or family and see more of the world. When planning, bundle your car rental and hotel into one discounted package to maximize savings on both. Or, leave room for spontaneity, booking what you need when you need it with our last-minute deals.

What to do on a road trip to Chicago?

When taking a road trip adventure, it’s best to plan how you want to spend your time on your road trip itinerary. We don’t want you to miss out on any of the best things to do in Chicago. You can book all the road trip activities on your Chicago wishlist, and even plan activities along your route as well.

How to rent a car for a road trip?

For an epic road trip, you'll need the perfect car. Renting a car for a road trip is the best option that doesn’t put miles or strain on your vehicle, and especially when it's also so affordable. Because when you book on Expedia, it doesn't need to be expensive. You can pick up a cheap car rental and head out to one of these incredible vacation rentals in Chicago. And when you bundle car rentals with hotel stays, you'll save even more on each part of your journey.

Frequently asked questions

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.

Bundling your hotel and flight with Expedia won’t just save valuable time — it’ll save you cash too. As much as $583, as a matter of fact! A Chicago vacation package makes it simple to put together the ideal trip. With more than 550 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.

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Chicago, IL Vacation Packages

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Chicago Vacation: Coronavirus Information

Top Chicago Flight + Hotel Deals

The Langham, Chicago

$642

Residence Inn Chicago Downtown/Loop

$439

Swissotel - Chicago

$516

DoubleTree by Hilton Chicago Midway Airport

$554

The Westin Chicago River North

$537

Where to stay in Chicago

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Hotels in Chicago

Top things to do in Chicago

Chicago CityPASS: Admission to Top 5 Chicago Attractions

360 CHICAGO Observation Deck (Hancock Center)

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

What are the advantages of a road trip to Chicago?

How to plan a road trip to Chicago?

What to do on a road trip to Chicago?

How to rent a car for a road trip?

Frequently asked questions

More trip options

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Flights

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