Chicago Vacation Packages

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Fully refundable rates on most hotels. Because flexibility matters

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Top Chicago Flight + Hotel Deals

Hyatt Regency Chicago
Kimpton Gray Hotel, an IHG Hotel
Kimpton Hotel Monaco Chicago, an IHG Hotel
Ambassador Chicago, part of JdV by Hyatt
The Langham, Chicago

Where to stay in Chicago

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

Top Hotels in Chicago

The Whitehall Hotel
The Whitehall Hotel
4 out of 5
105 E Delaware Pl, Chicago, IL, 60611
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Dec 23 to Dec 24
CA $110
per night
Dec 23 - Dec 24
3.9/5 Good! (3,165 reviews)
A cosy gem
"Great location.. lovely independent hotel just a sew steps off the Magnificent Mile. Cosy bar area and comfy beds. Decor in rooms is a little bit dated but otherwise a great choice and a refreshing change from the big hotel chains in the city."

Reviewed on Dec. 7, 2022

The Whitehall Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Jan 4 to Jan 5
CA $136
per night
Jan 4 - Jan 5
3.7/5 Good! (3,839 reviews)
"It was convenient and I enjoyed staying at an historic hotel like the Congress."

Reviewed on Dec. 8, 2022

Congress Plaza Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL, 60654
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Dec 12 to Dec 13
CA $122
per night
Dec 12 - Dec 13
4.1/5 Very Good! (1,840 reviews)
"Nice and comfy Beautiful view of the city very clean"

Reviewed on Dec. 7, 2022

Eurostars Magnificent Mile
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

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.
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.
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.
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.
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.
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.

Your guide to Chicago Vacations

From the Loop and Lake Michigan to baseball and blues, Chicago is a city that simply screams American style.

The Second City

Though Los Angeles is undeniably the country's second-largest spot, Chicago holds a special place in the collective heart of the United States. Since its founding in the early 19th century, this take-no-prisoners town has played host to gangsters and legends, presidents and pioneers, and some of the most iconic jazz and blues spots this side of the Mississippi. It's almost symbolic of the nation's fierce independence; despite the glossy updates to its shopping strips and tourist attractions, Chicago still operates with a bold, brash ethos.

A World-Class Destination

Believe the hype: packages for Chicago IL are every bit as exciting as those in Los Angeles and New York. The landscape may be different — Chicago's skyline tends toward the futuristic, for instance, and its upscale districts are uniquely vibrant — but the cultural attractions are on par with the world's best. This is, above all, a powerhouse of a city, and that no-holds-barred attitude is evident in everything from the art museums to the cutting-edge restaurants.

Beyond the Breeze

Of course, there's a reason they call it the Windy City. Thanks to its position on Lake Michigan, this metropolis is subject to a relatively constant breeze. The seasons here are clearly defined with scorching summers and freezing winters, so you'll generally find the most comfortable temps in the transitional periods. Don't discount those high-season months however: Some of the best packages and cheap deals are available on hotels in Chicago when the mercury moves into the extremes.

Top Things to See and Do

Unless you're staying for several weeks, you'll need a tightly coordinated itinerary to hit the hottest sights. Lincoln Park is the best spot for bustling beaches and gorgeous gardens, and its associated Lincoln Park Zoo is designed to make any animal lover swoon. Wrigley Field is a must for baseball fans, but head straight for Navy Pier when the sun goes down. The city's most effervescent clubs and restaurants are situated in the area, and you can easily head to the North Side for its iconic blues joints. If you rent a car in Chicago, set it aside for your downtown adventures. The L is more than sufficient.

Chicago Deals, Discounts, and More

Before you make a beeline for the city's borders, browse the travel tools at Expedia to find the latest holiday packages combining your accommodations and flight deals to Chicago. Chi-Town getaways have never looked so sweet.

Popular places to visit

Things to do