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All-Inclusive Hotels and Accommodations in Chicago

Finding the right all-inclusive accommodation for your trip to Chicago has never been so simple, and with the vast amount of choices on our site you're sure to find one that suits your needs. The closest major airport is in Chicago, IL (MDW-Midway Intl.), which is located 8.6 mi (13.9 km) from the city center. Chicago is known for shopping and culture, and offers a host of things to see and do such as Chicago Premium Outlets and Chicago Cultural Center. Look through our choice of all-inclusive accommodations where you can enjoy a host of amenities such as entertainment, kid's clubs, and of course food and beverages all included in your room rate. Many of our all-inclusive hotels also feature activities such as golf, yoga, water sports, and more, which you can enjoy without any additional cost. Expedia even has hotels with all-inclusive rooms and we have a varied list to choose from. If you have a few hotels in mind but need a little more time, you can save them to your favorites, so you don’t lose track of the best options for your vacation. From resorts to all-inclusive rooms, it's all right here, and it’s just a click away.

Planning Your Trip to Chicago

If you're curious about the best time to stay in Chicago, here is a summary of the weather throughout the year:

  • Hottest months: July, June, August, and September, with an average temperature of 83°F
  • Coldest months: January, February, December, and March, with an average temperature of 20°F
  • Driest months: February, January, December, and March, with an average rainfall of 2.31 inches
  • Rainiest months: May, June, July, and August, with an average rainfall of 4.05 inches

Sightseeing In and Around Chicago

Venture out to Chicago Premium Outlets and Chicago Cultural Center, and see why travelers like the shopping and cultural scene in Chicago. Other top attractions include Art Institute of Chicago, Millennium Park, and Willis Tower.

Chicago is also known for its:

  • Skyscrapers
  • Architecture
  • Art
  • Monuments
  • Museums
  • Entertainment

Getting Around Chicago

With so many ways to get around, seeing Chicago is simple. Nearby metro stations include Monroe Station, Monroe Station, and Adams-Wabash Station. If you want to see more of the area, hop aboard a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.

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Frequently asked questions

Looking for Chicago all-inclusive resorts?
Chicago is known for shopping and culture, and offers a host of things to see and do such as Navy Pier and Chicago Theatre. Browse our choice of all-inclusive hotel rooms where you can enjoy a good selection of amenities such as entertainment, kid’s clubs, and of course food and beverages all included in the price. Many of our all-inclusive resorts also feature activities such as golf, yoga, water sports, and more, which you can enjoy without any additional cost. The closest major airport is Chicago, IL (ORD-O’Hare Intl.), which is located 15.7 mi (25.3 km) away.
What's the weather like in Chicago?
The hottest months are usually July and June with an average temp of 72°F, while the coldest months are January and February with an average of 30°F. Average annual rainfall for Chicago is 39 inches.
What is Chicago famous for?
Venture out to Navy Pier and Chicago Theatre, and see why travelers like the shopping and cultural scene in Chicago. Other favorite attractions include Art Institute of Chicago, Millennium Park, and Willis Tower.
What's the best way to get around Chicago?
With so many transportation options, seeing Chicago is a breeze. Walk to nearby metro stations like Monroe Station (Red Line), Monroe Station (Blue Line), and Adams-Wabash Station. If you want to journey outside of the area, ride aboard a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.