Chicago Vacation Packages

More than just another big city, Chicago’s Midwestern soul will make you feel right at home.

Explore Chicago

Whether it’s your first time visiting or a weekend getaway, there are lots of ways to experience America’s Second City. Located on the southern tip of Lake Michigan, Chicago’s rich tapestry of neighborhoods each have their own personality and style — from Little Italy’s authentic Italian fare to the Magnificent Mile’s dizzying array of stores, restaurants and attractions. Chicago is home to some of the most unforgettable sights, including Willis Tower, AT&T Plaza Millennium Park and Wrigley Field.

Hugging Lake Michigan's shoreline, this 19-mile paved pathway gives outdoor enthusiasts access to many tourist attractions throughout the city.

The La Salle Street Bridge is one of only a few bascule bridges in Chicago constructed with four bridge tender house buildings.

Located in the heart of downtown, Millennium Park is an award-winning center for art, music, architecture and landscape design.

Chicago Lakefront Trail Slide 1 of 3: Hugging Lake Michigan's shoreline, this 19-mile paved pathway gives outdoor enthusiasts access to many tourist attractions throughout the city.
La Salle Street Bridge Slide 2 of 3: The La Salle Street Bridge is one of only a few bascule bridges in Chicago constructed with four bridge tender house buildings.
Millennium Park Slide 3 of 3: Located in the heart of downtown, Millennium Park is an award-winning center for art, music, architecture and landscape design.

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Chicago Activites

For a classic Chicago experience, take a spin on the 196-foot Ferris wheel at Navy Pier, or snap a selfie in front of Cloud Gate, also known as the Bean, a reflective steel sculpture and iconic landmark. Navy Pier extends over six city blocks, and is home to the Crystal Gardens, Chicago Children’s Museum, Chicago Shakespeare Theatre, amusement rides and more.

Make time to uncover some of Chicago’s best-kept secrets at underground venues, including cozy hangouts and hidden speakeasies. And sports fans will find the Cubs, White Sox, Bulls and Bears all play home games here.

All year long there are things to do and see, from a magical winter holiday market to summer music festivals to cool fall events along the river. Chicago is also known as a city in a garden because of its sprawling parks, hidden gardens, sandy beaches and lakefront trails.

Dining & Drinks

The number-one reason to visit Chicago is its great food scene. The dining options are endless, and just as good as the list is long. Chicago-style hot dogs, deep-dish pizza and the Italian beef sandwich are just a few of the amazing dishes you absolutely have to try.

Fine dining in Michelin-awarded restaurants run by star chefs feature celebrated cuisine — from Korean-American fusion to modern Midwestern fare. And this is just the beginning. After dinner, the options are endless. There are blues bars, dance clubs, outstanding performing arts theater, comedy clubs and more.

Getting to Chicago

Delta Vacations flight + hotel packages include round-trip airfare aboard Delta to O’Hare International Airport (ORD) or Midway Airport (MDW). To get into the city and to your hotel — car rentals, taxis and shared vans are available, as well as bus and train options.

Looking to book a flight + car package?

Car Rentals

National Premium Package

In the U.S., we offer the National Premium All-Inclusive Package. All insurance, taxes and surcharges are included. You have your choice of vehicles; up to five additional drivers are included at no extra charge; and the primary driver may earn up to 500 bonus miles per rental, plus an additional 200 bonus miles per rental day, through the SkyMiles^® Program.^†

Alamo^® Rent A Car, Enterprise^® Rent-A-Car and National^® Car Rental

Make the most of your vacation by exploring the U.S. with a rental car from Alamo, Enterprise or National. See the sights, take the family out to dinner, and explore all this fabulous destination has to offer with the freedom of a rental car. Plus, the primary driver may earn up to 500 bonus miles per rental and an additional 200 bonus miles per rental day, through the SkyMiles^® Program in the U.S. and Canada.^†

Check out our current, money-saving car rental offers, opens in a new window.

†Delta SkyMiles Membership number must be provided during pick up at the rental counter. The car must be rented in Member's name to earn mileage. Only one SkyMiles Member per car rental will be credited with miles. Offer valid for rentals picked up at participating Alamo or National Car Rental locations in the United States and Canada. Please allow 6 to 8 weeks after completed qualifying rental for miles to be posted to your account. Bonus miles not available with Enterprise car rentals worldwide and not available with Alamo or National rentals in the Caribbean and Mexico.

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VACATIONS, SIMPLIFIED

Choose from a curated selection of hotels, rides and activities, paired with your Delta® in-flight experience, with itineraries tailored to you and booked all in one place.

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Unlock exclusive offers and savings when you book everything together. Plus, use miles to pay for your vacation, earn MQDs toward Medallion® Status and earn miles on every vacation package.

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