Cheap Flights from Chicago

What the fares from Chicago look like right now

The cheapest trip found from Chicago for October 2026 was St. Louis at $117 return (Thu 15 Oct – Mon 19 Oct).
We found 40 destinations with prices and at least 12 hours on the ground, and 21 of them are non-stop.
Want to go further? Austin takes 12h 56m (1 stop) and costs $238.
Monthly trips in this list last 3–5 days, so most are long weekends. Use the live search to set exactly how many days you have.

Patterns in the fares from Chicago

Across the 40 destinations we found, return prices run from $117 to $757, with a median of $267.
They are spread over 3 countries.
Of the 15 cheapest trips, 9 leave on a Thursday.
21 of the 40 destinations (52%) come with a non-stop flight.
The longest non-stop flight in the list is Los Angeles (4h 50m), at $138.
Frontier offers the cheapest flight for 14 of the 40 destinations.
Best price per hour on the ground: St. Louis, 89 hours there for $117.

Cheap flights from Chicago in October 2026

Return prices per person, sorted by price. Only trips with at least 12 hours on the ground are listed.

Destination	Price	Flight	Dates	Time there
St. Louis, United States	$117	1h 19m · Non-stop	Thu 15 Oct – Mon 19 Oct	89h
Minneapolis, United States also: Saint Paul	$117	1h 33m · Non-stop	Thu 15 Oct – Mon 19 Oct	89h
Philadelphia, United States	$128	2h 23m · Non-stop	Sat 24 Oct – Mon 26 Oct	39h
Los Angeles, United States	$138	4h 50m · Non-stop	Sat 24 Oct – Mon 26 Oct	34h
Atlanta, United States	$148	2h 16m · Non-stop	Thu 29 Oct – Mon 2 Nov	87h
Miami, United States also: Fort Lauderdale, Miami Beach	$151	3h 08m · Non-stop	Sat 24 Oct – Mon 26 Oct	38h
Denver, United States also: Rocky Mountain National Park, Wind Cave National Park	$153	2h 49m · Non-stop	Thu 22 Oct – Mon 26 Oct	86h
Dallas, United States also: Fort Worth	$188	2h 39m · Non-stop	Thu 15 Oct – Mon 19 Oct	87h
Washington, D.C., United States also: Baltimore	$188	2h 03m · Non-stop	Thu 22 Oct – Mon 26 Oct	88h
Walt Disney World® Resort, United States also: Orlando	$190	4h 47m · 1 stop	Sat 24 Oct – Mon 26 Oct	34h
Detroit, United States	$197	1h 27m · Non-stop	Thu 15 Oct – Mon 19 Oct	89h
Houston, United States	$208	2h 59m · Non-stop	Thu 22 Oct – Mon 26 Oct	86h
Boston, United States	$215	2h 23m · Non-stop	Sat 24 Oct – Mon 26 Oct	39h
Bryce Canyon National Park, United States	$215	5h 21m · 1 stop	Sat 31 Oct – Mon 2 Nov	33h
Las Vegas, United States also: Zion National Park, Grand Canyon National Park	$228	4h 21m · Non-stop	Thu 29 Oct – Mon 2 Nov	83h

Prices are a snapshot from 21 September 2026 (source: Google Flights data) and change often. Check the live search before you book. “Time there” is the trip length minus the return flights and a 4-hour airport buffer; see how we calculate it.

Frequently asked questions

What are the cheapest flights from Chicago?

On 21 September 2026, the cheapest trip we found for October 2026 was St. Louis at $117 return. Prices change daily, so search live for today's fares.

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