Midwest & Chicago Vacation Packages, Resorts & Hotels

Midwest & Chicago Vacation Packages
$185+

The Drake Hotel - On Magnificent Mile
Historic hotel by Oak Street Beach

Classic elegance with modern comfort. Since 1920 this iconic hotel has set the bar for service and style for travelers visiting the city or staying for business. Boasting a choice location near the beginning of Magnificent Mile and offering views of both downtown Chicago and Lake Michigan, you'll be close to several attractions, shopping and dining venues. Onsite restaurant, lounge, convenience store, fitness room. Traveling with your 4-legged friends? No problem - The Drake is pet-friendly.


Midwest & Chicago Vacation Packages - Visit Chicago, Branson & the Dells

The midwestern states of the U.S. provide the vacation destinations of Chicago, Detroit, St. Louis, musical Branson, the waterparks of Wisconsin Dells and historic Mackinac Island where cars are not permitted. For more excitement, visit the rollercoaster capital of the world at Cedar Point near Sandusky, Ohio. Whatever your interest, here are some midwest and Chicago vacation packages to help you plan.



Tour the Windy City with Our Chicago Vacation Packages

Looking for fun Midwest vacations for your family? Look no further than our affordable Chicago vacation packages. Join the more than 50 million visitors who come to Chicago each year for tourism and vacations.

Chicago is packed to the brim with entertainment options. If you’re a fan of shopping, peruse the Magnificent Mile, Navy Pier, and State Street shopping areas to get a few upscale gifts for friends back home. You can also grab a bite to eat at one of the city’s highly-ranked restaurants, or even take a walking tour of the city’s architecture. Though the city is ranked the sixth most walkable in the United States, you can rest your tired feet by taking a ride on the famous L train that loops through the city above the streets.

Due to the tragic Great Chicago Fire, a huge building boom took place in the late 19th and early 20th century, creating one of the densest and tallest skylines in the world. There are many notable structures that combine innovation and experimentation, including the Aqua building, 35 East Wacker, the Chicago Board of Trade Building, the Chicago Cultural Center, and the Chicago Water Tower. It’s also home to some of the world’s tallest buildings, including the Willis Tower and the Trump International Hotel and Tower. Many Chicago tours can lead you through the streets while explaining the history and significance of these buildings.

One of the highlights of Chicago is Grant Park, which sits comfortably on the eastern side of Lake Michigan and offers spectacular views. Within this park is the famous Millennium Park, which is a 24.5-acre area that was created to celebrate the coming of the second millennium. In the park, you can gaze at the reflective Cloud Gate or admire the picturesque Crown Fountain.

For sports fans, stopping at Wrigley Field is a must. From there, you can spend the rest of your day watching animals at the Lincoln Park Zoo, learning new knowledge at the Museum of Science and Industry, or catching a performance by the Chicago Symphony Orchestra. The best way to see all of these sights is to choose one of our Chicago vacation packages, which will keep you organized and help you find a great Chicago hotel to stay in.

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