Vacation Packages from Chicago, IL

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Find Amazing Deals on Vacations from Chicago

Vacation packages from Chicago

Search our inventory of vacation deals to find the best vacation packages from Chicago. Whether you’re planning luxury trips or cheap vacations from Chicago, when you bundle flights or car rentals with your hotel you can earn savings. To book a cheap vacation package from Chicago, view our current offers! A good tip to save more is to stay flexible with dates, hotel location and amenities, flight details, and car rental types and providers so you can compare multiple options and get the best deals.


Plan a friends’ getaway with one of our vacation packages to Miami or head to the Big Apple with a package trip to New York. Book one of our vacation packages to Las Vegas for a few days of winning big.


Weekend packages from Chicago

We source amazing deals on weekend getaways from Chicago for all types of travelers. Book one of these romantic hotels in New York with your loved one, or plan a trip that the kids will love with one of our weekend family getaways from Chicago. Look out for our family-friendly filter!


During the cold months, take a quick flight south (perhaps Austin, Texas, or Miami, Florida) for warm weekend getaways from Chicago. And when you want to hit the slopes, there are various skiing and snowboard destinations nearby in Michigan for winter weekend getaways from Chicago.


Great road trips from Chicago

There are many options for good road trips from Chicago, including those to lakeshore towns in Michigan or Wisconsin. For an extended vacation, take a road trip from Chicago to New York, where you can relax after a day of exploring the city at your hotel with a spa or pool. No matter where your 2023 road trips from Chicago may take you, explore Expedia’s amazing car rental deals sourced from various providers—all at attractive prices.


Last-minute vacations from Chicago

Whether you’re looking for last-minute vacations from Chicago for tonight or next week, check out our last-minute vacation deals from Chicago to get the best price on a spontaneous couples’ trip, family vacation, and more. We’re your one-stop solution for hotel, flights, and car rental packages so that you can book your last-minute getaways from Chicago for the right price.


All-inclusive vacations from Chicago

Book an all-inclusive vacation from Chicago to exciting destinations. Take quick getaways from Chicago to the beach or longer trips to mountain towns or other large cities. For inspiration, check out our deals on all inclusive resorts across the US. To save more on your trip, bundle your travel into an all-inclusive vacation package from Chicago.


Flexibility and cancellation

Check “Free cancellations” or “No change fees” when planning your trip for flexibility. Some package bookings for getaways from Chicago are eligible for refunds, but check your itinerary to confirm. Visit our customer service portal for assistance.