RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → DFW
Chicago to Dallas
Best fare, round trip
$145
−49%
below its usual $285
you keep $140
RareFound
- Depart
- Thu 5 Nov
- Return
- Thu 12 Nov
- Stay
- 7 nights
- Flight
- 1 stop · 3.5h
- Airline
Southwest
Most of this route’s monthly lows fall between $223 and $285. The drop beats 95% of measured fares on the board, over 4 observed months.
Cached fare — the booking search re-prices live before you pay.
United StatesDallasAmerican’s fortress hub — which means almost everywhere connects, and Latin America is closer than the coasts.Best windowMar–May · Oct–NovAirportsDFW · Love Field (DAL)Every route into DallasFare seasonality
When this route gets cheap.
Fares bottom out in November around $145 and peak in October near $313, 116% dearer, across the 4 months we track. The cheapest itinerary we are tracking makes one stop and takes about 3.5 hours outbound, on a 7-night trip — ticketed under Southwest, which on a connecting fare need not operate every leg. At $145 for 1,295 km each way, that works out to about $56 per 1,000 km flown. That is above the $41 per 1,000 km typical of short-haul fares here. The best time to be in Dallas: Mar–May · Oct–Nov.
The 4 days we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 70% higher than when tracking began on 8 Aug — $186 then versus $317 now, across 19 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $124, on 3 Oct.
These are the only days we have a cached price for on this route so far — not the only days it flies. The search above covers any date.
Cached fares · checked 15 Oct 2026
Cheapest in Nov, around $145
49% below the $285 typical fare
$313Oct, above the usual price. Compare October fares.$145Nov, the cheapest month. Compare November fares.$223Dec, below the usual price. Compare December fares.$283Mar ’27, around the usual price. Compare March fares.
CheapestBelow usualUsualAbove usualPress a month to compare its fares
Cheapest round-trip fare found each month, Chicago to Dallas, from cached prices.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ DFW · Love Field (DAL)
- Flight time
- ≈3.5 hours outbound
- Distance
- ≈1,295 km each way
- Typical price
- $285 round-trip (seasonal median)
- Airlines on the board
- Southwest
- Itineraries
- Connections on current fares
- Best months to visit
- Mar–May · Oct–Nov
Good to know
CHI → DFW, answered.
Is $145 a good price for Chicago to Dallas?
Yes — the seasonal median for this route is around $285 round-trip. At $145 you're 49% below that, which we rate rare for this route.
What is the cheapest month to fly from Chicago to Dallas?
Across 4 months of cached-fare history, Nov comes out cheapest on this route. The best months to actually be in Dallas are Mar–May · Oct–Nov — when those overlap, that's your window.
How far in advance should I book CHI → Dallas?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. What we can measure is which month is cheap: across 4 months of cached fares, Nov comes out lowest on this route. Our guide Why flight prices change covers what does move a fare.
Are there nonstop flights from Chicago to Dallas?
The current cheapest fares involve a connection, ticketed under Southwest. We hold no nonstop fare on this route right now, which does not mean none flies — search your exact dates to see what does.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 17 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in Dallas?
Lock the flight first — then compare stays for 5–12 Nov · 7 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → DFW drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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