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Not ready to book? to track prices.Southwest flights from Chicago Midway Airport to Cleveland
Our best Southwest deals on Chicago Midway Airport to Cleveland flight tickets
Frontier flights from Chicago Midway Airport to Cleveland
Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
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Use the filters below to find and compare flights from Chicago Midway Airport to Cleveland that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Tue 11/10
6:42 pm-12:07 pm
1 stop16h 25m
Cleveland Hopkins Intl
Fri 11/13
3:21 pm-11:47 pm
1 stop9h 26m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Fri 11/6
6:42 pm-1:34 pm
1 stop17h 52m
Cleveland Hopkins Intl
Tue 11/10
6:35 am-5:47 pm
1 stop12h 12m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Tue 11/24
8:42 pm-8:41 am
1 stop10h 59m
Cleveland Hopkins Intl
Thu 12/3
6:00 am-2:55 pm
1 stop9h 55m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Sat 11/7
7:15 am-1:34 pm
1 stop5h 19m
Cleveland Hopkins Intl
Tue 11/10
6:35 am-5:47 pm
1 stop12h 12m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Fri 11/27
9:07 am-8:09 pm
1 stop10h 02m
Cleveland Hopkins Intl
Thu 12/3
6:00 am-2:55 pm
1 stop9h 55m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Thu 11/5
6:30 am-12:45 pm
1 stop5h 15m
Cleveland Hopkins Intl
Mon 11/9
5:35 pm-11:15 pm
1 stop6h 40m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Fri 11/6
6:10 pm-11:50 pm
1 stop4h 40m
Cleveland Hopkins Intl
Fri 11/13
8:55 pm-12:10 am
1 stop4h 15m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Wed 11/11
6:00 am-12:00 pm
1 stop5h 00m
Cleveland Hopkins Intl
Wed 11/11
3:50 pm-6:55 pm
1 stop4h 05m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Sun 11/1
6:16 am-8:20 pm
1 stop13h 04m
Cleveland Hopkins Intl
Mon 11/2
3:21 pm-11:47 pm
1 stop9h 26m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Thu 10/29
6:16 am-8:54 pm
1 stop13h 38m
Cleveland Hopkins Intl
Sun 11/1
6:35 am-11:47 pm
1 stop18h 12m
See travel insights to Cleveland from
How to get the cheapest flight ticket from Chicago Midway Airport to Cleveland
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Cleveland?
In general, November is the cheapest month to fly from Chicago Midway Airport to Cleveland. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you’re not able to fly to Cleveland in November, then May is your next best option. Flight prices from Chicago Midway Airport to Cleveland during May average around $234.
What is the cheapest day to depart on your flight to Cleveland?
The cheapest day to depart from Chicago Midway Airport to Cleveland is on a Saturday when prices can be found for as low as $266. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Cleveland on Sunday is $534.
What is the cheapest time of day to depart on your flight to Cleveland?
Our data shows that the cheapest Chicago Midway Airport to Cleveland flights are usually those with departure times at noon. Our users have found flights to Cleveland at noon for as low as $312. In contrast, the most expensive time of day to depart to Cleveland is in the evening when prices are around $472.
What is the cheapest Chicago Midway to Cleveland Hopkins Intl flight route?
Fly from Chicago Midway to Cleveland Hopkins Intl for the best Chicago Midway - Cleveland Hopkins Intl flight prices
What cabin class options are available on Chicago Midway Airport to Cleveland flights?
There is only 1 cabin class available to choose from on Chicago Midway Airport to Cleveland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago Midway Airport to Cleveland flights?
You could potentially save up to 59% on your flight if you consider stops on a Chicago Midway Airport to Cleveland flight.
How many flights depart from Chicago Midway Airport to Cleveland on average per day?
As of October 2026, there are 2 flights per day flying from Chicago Midway Airport to Cleveland. The most common time of day flights depart is 7:00AM, with 44% of flights taking off at noon.
How many flights depart from Chicago Midway Airport to Cleveland on average per week?
As of October 2026, 15 flights take off from Chicago Midway Airport and land in Cleveland each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
When to book flights from Chicago Midway Airport to Cleveland
Cheap Chicago Midway Airport to Cleveland (MDW to CLE) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Cleveland
Frequently asked questions about flying from Chicago Midway Airport to Cleveland
How far is Chicago Midway to Cleveland Hopkins Intl by plane?
Cleveland Hopkins Intl is 312.8 mi away from Chicago Midway. Typically, this will take 1h 10m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to Cleveland Hopkins Intl Airport?
Prices for flights from Chicago Midway Airport to Cleveland Hopkins Intl Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to Cleveland Hopkins Intl Airport?
As of October 2026, there is 1 operator available to choose from for flights from Chicago Midway Airport to Cleveland Hopkins Intl Airport.
How old do you have to be to fly from Chicago Midway Airport to Cleveland Hopkins Intl Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Cleveland Hopkins Intl Airport.
What documentation or ID do you need to fly to Cleveland Hopkins Intl Airport?
The required travel and health documents for your Cleveland Hopkins Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Cleveland Hopkins Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago Midway Airport to Cleveland?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Cleveland is Boeing 737 MAX 8, representing 13.95% of all bookings. The subsequent popular models are Boeing 737-800 at 12.89%, Embraer 175 (Enhanced Winglets) at 10.26%, and Boeing 737-900 at 8.95%.
What is the most popular airline from Chicago Midway Airport to Cleveland?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Cleveland is Southwest (100% of total bookings).
Best airlines flying from Chicago Midway Airport to Cleveland
Compare and see reviews for airlines that fly from Chicago Midway Airport to Cleveland with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $117 | Free Cancellation | Rating 7.9 4,222 reviews |
Southwest Flights From Chicago Midway Airport to Cleveland
Across 15 Southwest flights from Chicago Midway Airport to Cleveland this week, the average price was $509, with the best Southwest deals starting from $117 round-trip. 4,222 users have rated Southwest on momondo, with an average score of 7.9/10.
Traveling to a place near Cleveland?
Book flights to Cleveland if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Cleveland?
It is quick and easy to find Chicago to Cleveland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Cleveland that suits you.
Can I find flights from Chicago to Cleveland with flexible booking policies on momondo?
Yes. All flights to Cleveland from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Chicago to Cleveland?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Cleveland.
I’m not ready to book a flight from Chicago to Cleveland right now. Can momondo alert me if prices change?
Price alerts on flights to Cleveland from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.