starting at $114
starting at $129
starting at $56
starting at $106
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Cleveland to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A non-stop flight is the most convenient and comfortable way to fly from Cleveland to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
The only airline operating direct flights from Cleveland to Chicago is Southwest Airlines. Flights operate every day.
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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
More than 4 airlines operate flights from Cleveland to Chicago, including United Airlines, American Airlines, Southwest Airlines, and Frontier Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $56, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.
starting at $114
starting at $129
starting at $56
starting at $106
Cleveland — Chicago
10/17/2026
Departure
Direct flight
UA4748
starting at $114
Cleveland — Chicago
10/18/2026
Departure
Direct flight
UA2315
starting at $154
Cleveland — Chicago
09/07/2026
Departure
Direct flight
AA6363
starting at $408
Cleveland — Chicago
09/11/2026
Departure
Direct flight
WN2097
starting at $261
Cleveland — Chicago
09/12/2026
Departure
Direct flight
UA2443
starting at $203
Cleveland — Chicago
10/19/2026
Departure
Direct flight
UA4748
starting at $203
Cleveland — Chicago
10/20/2026
Departure
Direct flight
AA4360
starting at $129
Southwest Airlines
Every day
starting at $247
The cheapest one-way flight from Cleveland to Chicago departs on 10/20/2026, is operated by Southwest Airlines and costs $56
There is no information about the cheapest roundtrip flight from Cleveland to Chicago
Fastest flight from Cleveland to Chicago takes 1h 15m
There are direct flights on this route 5 days a week: Su, Mo, Tu, Fr, and Sa
The distance between Cleveland and Chicago is 494km (306 miles). The average flight duration is 1h 15m. There are 30 direct flights from Cleveland to Chicago. The time difference between Cleveland and Chicago is 1h. Flights from Cleveland begin at 8:20 AM. The latest flight from Cleveland departs at 8:10 PM
The cheapest flight ticket from Cleveland to Chicago according to data for the last 48 hours costs $56
Often the best time to buy tickets from Cleveland to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Cleveland to Chicago can be found flying in these months: October, September.
The fastest flights from Cleveland to Chicago start from 1 hour 15 minutes in the air.
The following airlines operate direct flights on the route Cleveland — Chicago: United Airlines, American Airlines, Southwest Airlines
The cost of a one-way flight from Cleveland to Chicago ranges from $101 (October 2026) to $118 (September 2026). On average, the ticket price is about $109–$118.
We couldn't find any special offers for flights from Cleveland to Chicago