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 → WAS
Chicago to Washington
Best fare, round trip
$154
−32%
below its usual $225
you keep $71
GreatFound
- Depart
- Fri 27 Nov
- Return
- Sun 29 Nov
- Stay
- 2 nights
- Flight
- 1 stop · 4h
- Airline
Frontier Airlines
Most of this route’s monthly lows fall between $204 and $227. The drop beats 81% of measured fares on the board, over 4 observed months.
Cached fare — the booking search re-prices live before you pay.
United StatesWashingtonFree museums by the dozen, and three airports competing hard enough to keep transatlantic fares honest.Best windowApr–May · Sep–OctAirportsDulles (IAD) · Reagan National (DCA) · Baltimore (BWI)Every route into WashingtonFare seasonality
When this route gets cheap.
Fares bottom out in November around $154 and peak in April near $409, 166% dearer, across the 4 months we track. The cheapest itinerary we are tracking makes one stop and takes about 4 hours outbound, on a 2-night trip — ticketed under Frontier Airlines, which on a connecting fare need not operate every leg. At $154 for 956 km each way, that works out to about $81 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 Washington: Apr–May · Sep–Oct.
Day-level prices for the next 4 months
Press a day to compare its fares
The median cached fare across this calendar is 19% higher than when tracking began on 8 Aug — $204 then versus $243 now, across 21 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 $116, on 31 Oct.
Cached day-level data for this route is sparse — 13 of 107 days priced, from 72 tracked fares. The days below are shown as found, with no cheapest-day or below-median call.
October 2026
November 2026
Sunday 1 November: $247. Compare fares from this day.234567891011Thursday 12 November: $239. Compare fares from this day.Friday 13 November: $243. Compare fares from this day.Saturday 14 November: $247. Compare fares from this day.151617181920212223Tuesday 24 November: $239. Compare fares from this day.25Thursday 26 November: $217. Compare fares from this day.Friday 27 November: $154. Compare fares from this day.282930
December 2026
12345678910111213141516171819202122232425262728293031
January 2027
12345678910111213Thursday 14 January: $227. Compare fares from this day.Friday 15 January: $305. Compare fares from this day.16171819202122232425262728293031
Cached fares · checked 17 Oct 2026
Cheapest in Nov, around $154
32% below the $225 typical fare
$204Oct, below the usual price. Compare October fares.$154Nov, the cheapest month. Compare November fares.$227Jan ’27, around the usual price. Compare January fares.$409Apr, above the usual price. Compare April fares.
CheapestBelow usualUsualAbove usualPress a month to compare its fares
Cheapest round-trip fare found each month, Chicago to Washington, from cached prices.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Dulles (IAD) · Reagan National (DCA) · Baltimore (BWI)
- Flight time
- ≈4 hours outbound
- Distance
- ≈956 km each way
- Typical price
- $225 round-trip (seasonal median)
- Airlines on the board
- Frontier Airlines
- Itineraries
- Connections on current fares
- Best months to visit
- Apr–May · Sep–Oct
Good to know
CHI → WAS, answered.
Is $154 a good price for Chicago to Washington?
Yes — the seasonal median for this route is around $225 round-trip. At $154 you're 32% below that, which we rate great for this route.
What is the cheapest month to fly from Chicago to Washington?
Across 4 months of cached-fare history, Nov comes out cheapest on this route. The best months to actually be in Washington are Apr–May · Sep–Oct — when those overlap, that's your window.
How far in advance should I book CHI → Washington?
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 Washington?
The current cheapest fares involve a connection, ticketed under Frontier Airlines. 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 Washington?
Lock the flight first — then compare stays for 27–29 Nov · 2 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → WAS drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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