Cheap Flights from Chicago to Maryland from £212 Return

Flight deals from Chicago to Maryland

Looking for a cheap last-minute deal or the best return flight from Chicago to Maryland? If you want to travel next month, return fares start from £322. Find the lowest prices on one-way and return tickets right here.

Hagerstown.£212 per passenger.Departing Fri, 3 Jul, returning Fri, 10 Jul.Return flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Fri, 3 Jul, arriving in Hagerstown.Inbound indirect flight with Allegiant Air, departs from Hagerstown on Fri, 10 Jul, arriving in Chicago Rockford.Price includes taxes and charges.From £212, select.

Salisbury.£322 per passenger.Departing Tue, 23 Jun, returning Mon, 29 Jun.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 23 Jun, arriving in Salisbury-Ocean City.Inbound indirect flight with Breeze Airways, departs from Salisbury-Ocean City on Mon, 29 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From £322, select.

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Flying from Chicago to Maryland

Arm yourself with these facts on the fly.

Cheapest flight found	£212
Cheapest month to fly	July
Cheapest airport to fly from	Chicago Rockford

How to find cheap flights from Chicago to Maryland

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Maryland. Other savvy travellers recently found return flights from £212 and one-way tickets from £110 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago Rockford into Hagerstown

At the moment, the lowest priced flight tickets to Maryland are from Chicago Rockford Airport to Hagerstown Airport.

Fly in July

We crunched the flight calendar and found the cheapest time to fly from Chicago to Maryland is currently July.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Maryland.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Maryland go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Maryland to Maryland flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Maryland flight price?

We looked at all of the upcoming return flights from Chicago to Maryland we could find over the next 12 months. It looks like £212 is the best price. This is good, compared to the average Maryland ticket price of £267.

What is the cheapest month to fly from Chicago to Maryland?

The cheapest month to fly from Chicago to Salisbury-Ocean City Airport is currently June. The cheapest month to fly from Chicago to Hagerstown Airport is usually July

Which upcoming date is cheapest to fly from Chicago to Maryland on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Maryland on Friday, 3 July 2026.

Are there any direct flights from Chicago to Maryland?

Currently, there aren't any direct flights from Chicago to Maryland, but you can still fly with a stopover.

If I'm flying from Chicago, where in Maryland is cheapest to fly into?

If you're flying from Chicago, the cheapest city in Maryland to fly into is Hagerstown. The cheapest airport serving Hagerstown at the moment is Hagerstown.