Chicago to Chesapeake Flights (CHI-PHF) from $79
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Selected fares from Chicago to Chesapeake
The cheapest prices found with in the last 7 days for return flights were $154 and $79 for one-way flights to Chesapeake for the period specified. Prices and availability are subject to change. Additional terms apply.
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Tips for booking flights from Chicago to Chesapeake on Travelocity
Make booking your trip from Chicago to Chesapeake a breeze with Travelocity's handy filters. Select whether you'd like a direct, one-stop, or multi-stop flight, only show specific airlines, and much more: It's never been so easy to tailor your journey to your preferences. Traveling with kids often means lots of luggage—so think about what baggage allowance you might need, and use the handy check-box filter to restrict your results to those with free carry-on luggage, for instance. Little ones can struggle with late-night departures or early-morning arrivals as well, so consider narrowing down your preferred arrival and departure times (yes, there's a filter for that, too) to align your travel with your family's schedule.
Flying from Chicago to Chesapeake: What you need to know
How to get cheap flights from Chicago to Chesapeake?
Booking well in advance is one of the easiest ways to cut the cost of your journey from Chicago to Chesapeake. In most cases, the further ahead you book, the cheaper flights tend to be. Consider traveling in the off-season, too, when prices are often lower across the board. For flights to Chesapeake, the cheapest month is usually September.* Great value flights can be had on this route departing from Chicago—and Travelocity's wide range of options is sure to include one that works for your family.
When is the cheapest time to travel from Chicago to Chesapeake?
Generally speaking, flights from Chicago to Chesapeake are usually cheapest in September.* In other words, that's the month to travel if you're looking to save on your adventure. Don't forget that flights are often cheaper if you book them in advance, too: Planning your travel well ahead of time is a great way to keep the cost of your family vacation low.
How far in advance can I book a flight from Chicago to Chesapeake?
Bookings for flights from Chicago to Chesapeake generally open 12 months in advance. If you're an early bird and book as soon as your date opens, that means you have a full year to sort out all the reservations for your hotel, hire car, and family-friendly vacation activities. Sometimes time's a bit tighter—but rest assured that you'll often still be able to find last-minute flights from Chicago to Chesapeake right up to the day that your plane is due to take off.
Is it better to book return or one-way flights from Chicago to Chesapeake?
Whether you book one-way or return flights is a question of personal preference. Often, booking return flights can be a cheaper option. For instance, round-trip flights from Chicago to Chesapeake in 2025 are available from as little as from $154, while one-way journeys start at from $79.* However, one-way flights give you the freedom to travel back from a different city or book your return leg at a later point in time, so you can shape your trip to suit you and your family.
Why should I use Travelocity to book flights from Chicago to Chesapeake?
When you book with Travelocity, you can choose from a large selection of airlines for your trip from Chicago to Chesapeake. With such an array to choose from, you're sure to find one that works for the whole family. Plus, many Travelocity flight bookings come with free cancellation—and should you need a helping hand, the customer service team is available 24/7 to assist you.
*Prices reflect current offers and availability is subject to change. Additional terms may apply.