$109 Cheap Delta flights from Cleveland to Chicago (CLE to MDW)

Find The Best Day To Fly from Cleveland to Chicago

Amazing Delta CLE to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $204 round trip and $109 one way. Prices and availability subject to change. Additional terms may apply.

MDW From CLE Economy Coach Packages on Similar Airlines

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Frequently asked questions

Can I catch a flight from Hopkins Intl. Airport (CLE) to Chicago Airport right now?
For info on any current MDW quarantine requirements and travel advice, visit our Covid-19 Travel Advisor. Look before you arrange your flight, so you don’t get caught up en route.
What terminal is Delta Air Lines at Hopkins Intl. Airport (CLE)?
Your boarding pass should tell you which terminal your Delta Air Lines flight will be boarding from at CLE. It might also be able to give you the arrival details for Chicago Airport. If not, it’s probably a wise idea to consult your airline.
Are there Delta Air Lines non-stop flights from CLE to MDW?
There aren’t any direct flights with Delta Air Lines from Cleveland Hopkins Intl. Airport to Midway Airport. But think of it this way — you can use the time to wander around and stretch those legs before jumping on your connecting flight.
How long is a Delta Air Lines flight from CLE to MDW?
If conditions are good and things go according to plan, your Delta Air Lines flight from CLE to MDW should take roughly 3 hours and 48 minutes. Take advantage of that short flight to go over the details of your travel schedule before you come in to land.
How many direct and indirect flights does Delta Air Lines fly from CLE to MDW?
Delta Air Lines is currently operating around 3 flights daily from Hopkins Intl. Airport (CLE) to Chicago Airport.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to MDW, please visit our Customer Service Portal.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Discover our best Delta flight from Cleveland CLE to Chicago MDW 

To find the best deals on flights to Cleveland from Chicago with Delta, just enter your travel dates, filter by Delta, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Cleveland CLE to Chicago MDW with Delta 

If you’re planning a round trip, booking return flights with Delta is usually the most cost-effective option. With airfares ranging from $204 to $217, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way Delta flights from Cleveland CLE to Chicago MDW 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way Delta flight from Cleveland to Chicago costs from $109. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to Chicago MDW from  Cleveland CLE with Delta 

To find a cheap Delta flight from Cleveland CLE to Chicago MDW, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on Delta flights from Cleveland CLE to Chicago MDW 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as August, or if you book a flight with a stopover. 

 

Find nonstop flights from Cleveland CLE to Chicago MDW with Delta 

If you’re keen to be on Chicago soil fast, don’t waste time with a stopover—filter your search results to show direct Delta flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for Delta flights from Cleveland CLE to Chicago MDW 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to Chicago MDW from  Cleveland CLE with Delta on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

Delta Airports
Hop on a(n) Delta flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
ATLUSAHartsfield-Jackson Atlanta Intl.252
DTWUSADetroit Metropolitan Wayne County156
MSPUSAMinneapolis - St. Paul Intl.131
SLCUSASalt Lake City Intl.116
SEAUSASeattle - Tacoma Intl.57
LAXUSALos Angeles Intl.41
AMSNLDSchiphol31
YYCCANCalgary Intl.26
YYZCANPearson Intl.24
JFKUSAJohn F. Kennedy Intl.23

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