$59 Find Cheap Flights from Cleveland to Chicago - Compare and Save

If you’ll be arriving at Chicago Midway International Airport (MDW) from CLE, there’s a road system linking the terminal and the secure area. You can easily move from one building to another via a pedestrian bridge after clearing with the security in the terminal building as you head to the concourse.

Those arriving with kids at Chicago O’Hare International Airport (ORD) from CLE will find nursing suites for use at this property. You can locate them at the Rotunda in Terminal 3, and in Terminal 2, Concourse F. Also, they have sinks, chairs, and power sockets.

Downtown Chicago is approximately 11 miles from MDW. There are numerous public transportation options linking the two points. However, the best way to travel between the two points is via the Orange Line train which covers the stretch in about 20-25min.

Many rental car agencies are located at the O'Hare International Airport (ORD). From the arrival, head to Suite 830, or at Routes Car & Truck Rentals near Schiller Park to pick up your car. Book in advance to enjoy special rates.

Among airlines operating Cleveland to Chicago flights:

• United Airlines: offers extra legroom; offers free seat selection
• Southwest: offers free seat selection
• American Airlines: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

3 airlines operate flights between Cleveland and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines
• Southwest

Flights from Cleveland to Chicago usually depart from Cleveland Hopkins Intl (CLE) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag and a checked bag in Economy Class
• Southwest: a cabin bag and a checked bag in Economy Class
• American Airlines: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Three cabin classes are available on flights from Cleveland to Chicago:

• Economy Class
• Business Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $175 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $272 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

One-stop flights from Cleveland to Chicago most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 72% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 21% of one-stop connections
• Fort Lauderdale (FLL) - 7% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

On the Cleveland to Chicago route, being flexible with your departure day can save you up to 22%. Saturday is the cheapest day at $246 round-trip on average, while Monday is the most expensive at $315: a $69 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Morning is the busiest departure period on Cleveland to Chicago flights, with 39% of flights leaving in that window. Afternoon departures account for 34%, evening flights for 27%, and night flights for 0%.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

These are the earliest and latest flight times available from Cleveland to Chicago:

• Earliest: departs at 5:00 am and lands at 6:40 am
• Latest: departs at 9:40 pm and lands at 11:20 pm.

The flight takes about 1h 40m.

Last-minute fares on this route - booked within 2 weeks of departure - run 95% above the route average of $271. Book 19 weeks before departure for the lowest fares.

A nonstop flight from Cleveland to Chicago takes 1h 40m, covering 300 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $117 to $972. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Cleveland to Chicago are currently lower than usual. Average one-way flight prices are about $63, which is 71% below the typical average for this route.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 22m, compared with 8h 25m via Atlanta Hartsfield-Jackson (ATL) and 19h 26m via Fort Lauderdale (FLL).

Chicago is 1 hour behind Cleveland (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

· Routes Car & Truck Rentals
· Europcar
· Hertz
· Dollar
· Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

· Alamo
· Enterprise Rent-A-Car
· Budget
· Avis
· National

Round-trip flights from Cleveland to Chicago range from $208 to $390, with an average of $271 over the past 12 months. Anything below $208 counts as a good deal.

Two airlines offer in-flight Wi-Fi on Cleveland to Chicago flights:

• • American Airlines
• • JetBlue