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One-Way Flights to Chicago

Updated 2026-03-13

From

$40

one-way

Current One-Way Deals to Chicago

RoutePriceBook
Miami (MIA) → Chicago (ORD)$40 View →

Prices are for one-way flights. Links may earn us a commission at no cost to you.

Average One-Way Prices to Chicago

JanFebMarAprMayJunJulAugSepOctNovDec
$79 $69 $65 $75 $79 $89 $95 $89 $69 $65 $75 $99

Cheapest month: Mar (avg $65). Prices are average one-way fares based on historical data.

How to Find Cheap One-Way Flights to Chicago

Chicago has two airports — O'Hare (ORD) for most airlines and Midway (MDW) for Southwest and budget carriers. Always compare both. Southwest dominates the budget market at Midway with free checked bags and no change fees. Frontier and Spirit fly into O'Hare with rock-bottom fares. For the cheapest one-way flights, fly midweek. The best deals appear from the West Coast (LA, SF) and South (Dallas, Houston, Atlanta). September and February consistently have the lowest fares. Avoid Thanksgiving, Christmas, and Lollapalooza weekend (August) for best prices.

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Frequently Asked Questions

How much is a one-way flight to Chicago?
One-way flights to Chicago range from $49–$150 from most US cities. Budget carriers like Frontier and Spirit regularly offer fares under $60. Southwest at Midway includes free bags.
What's the cheapest airline to fly to Chicago?
Frontier and Spirit (O'Hare) have the lowest base fares. Southwest (Midway) is great value with free checked bags. American and United compete from their hubs with occasional deals.
When is the cheapest time to fly to Chicago?
February, September, and October are the cheapest months. Winter is cold but fares are low. Avoid summer holidays and major event weekends for the best one-way prices.
Should I fly into O'Hare or Midway?
Midway is cheaper for budget carriers (especially Southwest) and closer to downtown. O'Hare has more airline options. Always compare both — the same route can be $30-50 cheaper at one vs. the other.

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