Can I travel to Chicago right now?

For all the up-to-date facts about visiting Chicago, head to our Covid-19 Travel Advisor . From travel restrictions to quarantine policies and more, this guide will help make your vacation as stress-free as possible.

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 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.

Chicago Vacation Packages | Holiday Packages & Trips 2021/2022

Reviewed on May 31, 2021

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!(725 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 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.

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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

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free cancellationReserve now, pay when you stay

3.7/5Good! (4,632 reviews)

"I like the location of the hotel but don't like the parking too much money"

Reviewed on Jun. 10, 2021

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St, Chicago, IL

Free cancellationReserve now, pay when you stay

4.1/5Very Good! (1,325 reviews)

"Nice area."

Reviewed on Jun. 9, 2021

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

Free cancellationReserve now, pay when you stay

4.4/5Excellent! (3,207 reviews)

"Bad parking. No valet"

Reviewed on Jun. 6, 2021

See all 2725 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 Mob Tour: Criminals & Gangsters Bus Tour

CA $57

Per adult

90% of travellers recommend

Chicago Hop-On Hop-Off Big Bus Tour

CA $61

Per adult

88% of travellers recommend

Chicago CityPASS: Admission to Top 5 Chicago Attractions

CA $137

Per adult

94% of travellers recommend

See all activities in Chicago

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.

Chicago Vacation Packages

Travellers

Room 1

Top Chicago Flight + Hotel Deals

Renaissance Chicago Downtown Hotel

CA $680

Residence Inn Chicago Downtown/Loop

CA $707

The Langham, Chicago

CA $1,040

The Godfrey Hotel Chicago

CA $643

The Peninsula Chicago

CA $1,224

Where to stay in Chicago

Downtown Chicago

Magnificent Mile

The Loop

Lincoln Park

Gold Coast

Top Hotels in Chicago

Top things to do in Chicago

Chicago Mob Tour: Criminals & Gangsters Bus Tour

Chicago Hop-On Hop-Off Big Bus Tour

Chicago CityPASS: Admission to Top 5 Chicago Attractions

Frequently asked questions

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