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.
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.
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.
How do I find weekend flights from Chicago for specific dates?
Use the live search: choose Chicago (ORD) as your departure airport, pick a date or a month, and set how many days you have. It shows every destination you can reach and what it costs.
How do you calculate time at the destination?
We take the trip length, subtract the return flights and a 4-hour airport buffer, and show what is left. Trips with under 12 hours on the ground are hidden by default.
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