Cleveland to Chicago: what the flight costs
In the last 60 days we checked this route 12 times. The typical return was £446 per person and the lowest £292, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £292 |
| Typical (median) | £446 |
| Price checks, 60 days | 12 |
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Trips we picked on this route
Just found · from ClevelandLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $394 per person, $221 below the typical fare on this route
- Hyatt Place in The Loop scores 8.2 from 1,959 reviews
- Free cancellation at Hyatt Place, and Sunday looks clear at 65°F
£1,238 for two · 2 nights · flights, hotel, taxes & fees
Flights £594 + hotel £644, taxes in · a checked bag each adds about £181
Frontier · with a stop · 12h 31m
The catch: The Frontier fare has one stop and takes 12h 31m on the way out for a 307-mile trip, and a checked bag is about $240 for two.
Worth it if a full travel day Friday is fine for this price; skip it if you'd rather pay $573 per person for the 1h 37m nonstop.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 15 Oct 2026 | 30 Oct – 1 Nov 2026 | £485 | UA | nonstop | 1h 40m | Kiwi.com |
| 15 Oct 2026 | 23 – 25 Oct 2026 | £332 | F9 | with a stop | 30h 15m | Kiwi.com |
| 15 Oct 2026 | 23 – 25 Oct 2026 | £292 | Frontier | with a stop | 12h 31m | Google Flights |
| 15 Oct 2026 | 30 Oct – 1 Nov 2026 | £487 | UA | nonstop | 1h 39m | Kiwi.com |
| 15 Oct 2026 | 23 – 25 Oct 2026 | £356 | F9 | with a stop | 8h 39m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £297 | Frontier | with a stop | 12h 31m | Google Flights |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £466 | UA | nonstop | 1h 36m | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £464 | UA | nonstop | 1h 36m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £429 | UA | nonstop | 1h 36m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £464 | UA | nonstop | 1h 36m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £366 | F9 | with a stop | 8h 39m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £464 | UA | nonstop | 1h 36m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about Cleveland to Chicago
What does a return from Cleveland to Chicago usually cost?
Over the last 60 days the typical price we found was £446 per person, taxes and fees included, across 12 checks; the lowest was £292.
When is the best time to fly from Cleveland to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from Cleveland to Chicago?
No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
Prices converted from US dollars at the rate of 15 Oct 2026.