Skyscanner

Cheap flights from Cleveland Hopkins International to Chicago Midway

Travelers and cabin class

Compare Cleveland Hopkins International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

TrustScore 4.5 out of 5 4.5 out of 5 based on 703 reviews Trustpilot

Flight deals from Cleveland Hopkins International to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from Cleveland Hopkins International to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$107 per passenger.Departing Tue, Jul 8, returning Wed, Jul 9.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Cleveland Hopkins International on Tue, Jul 8, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Wed, Jul 9, arriving in Cleveland Hopkins International.Price includes taxes and charges.From C$107, select.
Chicago.C$107 per passenger.Departing Wed, Jul 30, returning Tue, Aug 5.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Cleveland Hopkins International on Wed, Jul 30, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Aug 5, arriving in Cleveland Hopkins International.Price includes taxes and charges.From C$107, select.
Chicago.C$107 per passenger.Departing Tue, Jun 10, returning Wed, Jun 11.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Cleveland Hopkins International on Tue, Jun 10, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Wed, Jun 11, arriving in Cleveland Hopkins International.Price includes taxes and charges.From C$107, select.
Chicago.C$159 per passenger.Departing Wed, Aug 27, returning Mon, Sep 1.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Cleveland Hopkins International on Wed, Aug 27, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Sep 1, arriving in Cleveland Hopkins International.Price includes taxes and charges.From C$159, select.
Chicago.C$159 per passenger.Departing Wed, Aug 27, returning Sat, Aug 30.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Cleveland Hopkins International on Wed, Aug 27, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Aug 30, arriving in Cleveland Hopkins International.Price includes taxes and charges.From C$159, select.
Chicago.C$160 per passenger.Departing Wed, Sep 17, returning Sat, Sep 20.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Cleveland Hopkins International on Wed, Sep 17, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Sep 20, arriving in Cleveland Hopkins International.Price includes taxes and charges.From C$160, select.
Chicago.C$174 per passenger.Departing Sat, Oct 4, returning Tue, Oct 7.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Cleveland Hopkins International on Sat, Oct 4, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Tue, Oct 7, arriving in Cleveland Hopkins International.Price includes taxes and charges.From C$174, select.
Chicago.C$191 per passenger.Departing Wed, Jun 25, returning Sat, Jul 5.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Cleveland Hopkins International on Wed, Jun 25, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Jul 5, arriving in Cleveland Hopkins International.Price includes taxes and charges.From C$191, select.

Find the cheapest month to fly from Cleveland Hopkins International to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Cleveland Hopkins International to Chicago Midway flights are currently cheapest in June.
May
from C$251
Jun
from C$107
Jul
from C$107
Aug
from C$159
Sep
from C$160
Oct
from C$174
Nov
from C$237
Dec
from C$456
Jan
Find prices
Feb
Find prices
Mar
from C$501
Apr
Find prices

Direct flights from Cleveland Hopkins International to Chicago Midway

Cleveland Hopkins International to Chicago Midway: Alternative routes

Compare routes from Cleveland Hopkins International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Cleveland to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$107
Cheapest month to flyJuly
Average flight time1 hr, 20 mins
Most popular airlineSouthwest Airlines
Average flights per week21

Finding cheap flights from Cleveland Hopkins International to Chicago Midway: Frequently asked questions

The best price we found for a round-trip flight from Cleveland Hopkins International to Chicago Midway is C$107. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 20 minutes is the average flight time from Cleveland Hopkins International to Chicago Midway.
Southwest Airlines flies direct from Cleveland Hopkins International to Chicago Midway.
There are 21 flights per week flying from Cleveland Hopkins International to Chicago Midway, as of May 2025.
The cheapest month to fly from Cleveland Hopkins International to Chicago Midway is usually May 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Cleveland Hopkins International Airport to Chicago Midway Airport on Tuesday, July 8, 2025.
Yes – the average flight time is 1 hour and 20 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Cleveland Hopkins International Airport (CLE) to Chicago Midway International Airport (MDW): what you need to know

  • Around 1 hour 15 minutes is how long you can expect to be in the air on a direct flight from Cleveland Hopkins International Airport to Chicago Midway International Airport.

  • The timezone in Chicago is UTC-5, which is one hour behind Cleveland.

  • Choose from 17 weekly Cleveland Hopkins International Airport to Chicago Midway International Airport flights. The 06:10 departure with Southwest Airlines is the earliest flight you can take. Southwest Airlines operates the latest service of the day at 21:40.

  • Arrive at the airport on time so you don't miss your CLE to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the stress of rushing.

  • Travelling during a peak month such as July? School holidays and other popular periods can result in longer queues and delays at security. Be extra cautious and get there up to four hours ahead of an international flight and two hours before domestic departures.

  • Getting to Chicago (and then exploring more of United States!) is a snap with Southwest Airlines. This popular airline offers direct flights from Cleveland Hopkins International Airport to Chicago Midway International Airport.

  • The majority of travellers choose to travel with Southwest Airlines on this route.

  • Southwest Airlines is the most punctual carrier operating CLE to MDW flights, with 77.91% of its services arriving as planned.

  • Think about adding a stopover when booking your ticket from Cleveland Hopkins International Airport to Chicago Midway International Airport. Just deselect 'Direct flights only' to break up your trip, or visit a new city along the way. Check out these options between CLE and MDW:

    • Detroit Metropolitan Wayne County Airport

    • Nashville International Airport

    • Lambert-St. Louis International Airport

How to find the cheapest flights from Cleveland Hopkins International Airport (CLE) to Chicago Midway International Airport (MDW)

  • The cheapest price we've seen for a one-way Cleveland Hopkins International Airport to Chicago Midway International Airport flight is C$54. A return fare right now is C$107. Depending on the availability and when you book, these fares may change.

  • Score cheap tickets from CLE to MDW by booking six months ahead. Based on our research, that's the sweet spot for finding the biggest deals.

  • The cheapest month for flights from Cleveland Hopkins International Airport to Chicago Midway International Airport is May. Use the 'Whole month' tool to see the lowest prices if you have a flexible travel schedule.

  • Snapping up cheap flights from CLE to MDW is easy with Price Alerts. Simply set up one of these automatic alerts and we'll let you know when a new discounted fare appears.

  • Find the perfect flight for you with the help of the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Cleveland Hopkins International Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter by departure and arrival times, airline, and number of stops.

Handy information about Cleveland Hopkins International Airport (CLE)

  • CLE is located at 5300 Riverside Drive.

  • 76.58% of flights taking off from Cleveland Hopkins International Airport make it to their destination on schedule.

  • Central Cleveland to Cleveland Hopkins International Airport is around 24 kilometres. Depending on traffic, it'll take about 25 minutes to get there if you're catching a cab, ride-sharing or driving.

  • You can expect a journey time of around 1 hour 25 minutes on public transport.

  • Looking for a handy hotel near CLE? If you've booked an early flight from Cleveland Hopkins International Airport to Chicago Midway International Airport, these stays will put you moments from your departure lounge:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you want is a lengthy journey to your hotel if you're getting in late on a Cleveland Hopkins International Airport to Chicago Midway International Airport flight. Check in to one of these accommodation options near MDW instead:

  • Fast-track your adventure by picking up a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget to explore Chicago and beyond.

  • Reserving your ride from Chicago Midway International Airport around four weeks ahead gives you the best chance of locking in a great deal.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway International Airport is approximately 19 kilometres from the centre of Chicago. The drive time takes around 20 minutes.

  • Getting to the centre by public transport takes roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from Cleveland Hopkins International Airport to Chicago Midway International Airport is May, while July is the most popular. Pick the ideal time to visit Chicago based on whether you prefer a more relaxed vibe or a faster pace.

  • Lock in your flight from Cleveland Hopkins International Airport to Chicago Midway International Airport for July if you want to visit Chicago during its warmest month. Expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

  • Look for cheap tickets from CLE to MDW in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of United States

  • You've seen Chicago, now it's time to discover other parts of United States. Journey about 451 kilometres south-east to Columbus to check off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you on the go.

  • If you want to check out another great destination in United States, head for Indianapolis, about 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are among its highlights.

Plan the rest of your trip from Cleveland to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.