Chicago Holidays

You'll find cheap prices on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Chicago costs.

December, January and February are the best times to look for cheap Chicago holiday packages. Opting to travel in quieter periods means you'll typically find lower prices on accommodation and flights.

To fully enjoy a Chicago holiday, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighbourhoods like Central Chicago and Near North Side. If you've got some spare time, include a day trip or tour in your Chicago holiday itinerary.

Chicago has everything you need for a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field, or take the road less traveled, you'll find plenty to do on your Chicago holiday.

Use Expedia's filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.

Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a customised Chicago holiday by choosing your favourite accommodation type, airline and car class.

Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.

1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago.
2. Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that's an affordable stay or a swankier getaway.
3. Work out your trip length: Consider how long you'd like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chicago holiday package that brings all your bookings together.