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 → IST
Chicago to Istanbul
Best fare, round trip
$730
−12%
below its usual $830
you keep $100
Found
- Depart
- Sun 17 Jan
- Return
- Sun 31 Jan
- Stay
- 14 nights
- Flight
- 3 stops · 14h
- Airline
SAS
Most of this route’s monthly lows fall between $745 and $902. The drop beats 29% of measured fares on the board, over 8 observed months.
Cached fare — the booking search re-prices live before you pay.
TürkiyeIstanbulTwo continents, one skyline of minarets. Turkish Airlines’ mega-hub means constant fare battles.Best windowApr–May · Sep–OctAirportsIstanbul (IST) · Sabiha Gökçen (SAW)Every route into IstanbulFare seasonality
When this route gets cheap.
Fares bottom out in January around $730 and peak in May near $957, 31% dearer, across the 8 months we track. The cheapest itinerary we are tracking makes 3 stops and takes about 14 hours outbound, on a 14-night trip — ticketed under SAS, which on a connecting fare need not operate every leg. At $730 for 8,813 km each way, that works out to about $41 per 1,000 km flown. That is below the $44 per 1,000 km typical of long-haul fares here. Across the 20 departure cities we track at a similar distance from Istanbul, this fare ranks 13th — 1.9× the $390 we hold from Seoul. That puts it in the cheaper half of the 35 routes of similar length we watch out of Chicago, where the middle fare is $734. The best time to be in Istanbul: Apr–May · Sep–Oct.
Cheapest day in the next 4 months: 17 Jan '27, $730
Press a day to compare its fares
The median cached fare across this calendar is 7% higher than when tracking began on 8 Aug — $873 then versus $936 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 $486, on 21 Oct.
October 2026
1516Saturday 17 October: $1.1k, around the usual price. Compare fares from this day.Sunday 18 October: $978, around the usual price. Compare fares from this day.Monday 19 October: $1k, around the usual price. Compare fares from this day.Tuesday 20 October: $1k, around the usual price. Compare fares from this day.2122Friday 23 October: $1k, around the usual price. Compare fares from this day.Saturday 24 October: $1.2k, above the usual price. Compare fares from this day.Sunday 25 October: $1k, around the usual price. Compare fares from this day.Monday 26 October: $936, around the usual price. Compare fares from this day.272829Friday 30 October: $902, around the usual price. Compare fares from this day.31
November 2026
1Monday 2 November: $796, below the usual price. Compare fares from this day.345678910111213Saturday 14 November: $791, below the usual price. Compare fares from this day.Sunday 15 November: $847, below the usual price. Compare fares from this day.Monday 16 November: $772, below the usual price. Compare fares from this day.171819Friday 20 November: $1.3k, above the usual price. Compare fares from this day.2122Monday 23 November: $1.2k, above the usual price. Compare fares from this day.2425Thursday 26 November: $1k, around the usual price. Compare fares from this day.27282930
December 2026
Tuesday 1 December: $870, below the usual price. Compare fares from this day.23456Monday 7 December: $745, below the usual price. Compare fares from this day.89101112131415Wednesday 16 December: $1.1k, around the usual price. Compare fares from this day.171819Sunday 20 December: $1.5k, above the usual price. Compare fares from this day.Monday 21 December: $1.7k, above the usual price. Compare fares from this day.Tuesday 22 December: $1.6k, above the usual price. Compare fares from this day.23Thursday 24 December: $986, around the usual price. Compare fares from this day.Friday 25 December: $1.3k, above the usual price. Compare fares from this day.Saturday 26 December: $807, below the usual price. Compare fares from this day.Sunday 27 December: $835, below the usual price. Compare fares from this day.Monday 28 December: $745, below the usual price. Compare fares from this day.293031
January 2027
123Monday 4 January: $851, below the usual price. Compare fares from this day.5Wednesday 6 January: $851, below the usual price. Compare fares from this day.78910Monday 11 January: $747, below the usual price. Compare fares from this day.Tuesday 12 January: $779, below the usual price. Compare fares from this day.13141516Sunday 17 January: $730, the cheapest day in view. Compare fares from this day.Monday 18 January: $807, below the usual price. Compare fares from this day.19202122232425262728293031
CheapestBelow usualUsualAbove usualCached fares · checked 15 Oct 2026 · bands from 159 tracked fares
Cheapest in Jan, around $730
12% below the $830 typical fare
$902Oct, above the usual price. Compare October fares.$772Nov, below the usual price. Compare November fares.$745Dec, below the usual price. Compare December fares.$730Jan ’27, the cheapest month. Compare January fares.$745Feb, below the usual price. Compare February fares.$831Apr, around the usual price. Compare April fares.$957May, above the usual price. Compare May fares.$903Jul, above the usual price. Compare July fares.
CheapestBelow usualUsualAbove usualPress a month to compare its fares
Cheapest round-trip fare found each month, Chicago to Istanbul, from cached prices.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Istanbul (IST) · Sabiha Gökçen (SAW)
- Flight time
- ≈14 hours outbound
- Distance
- ≈8,813 km each way
- Typical price
- $830 round-trip (seasonal median)
- Airlines on the board
- SAS
- Itineraries
- Connections on current fares
- Best months to visit
- Apr–May · Sep–Oct
Good to know
CHI → IST, answered.
Is $730 a good price for Chicago to Istanbul?
Only slightly. The seasonal median is around $830 round-trip and this fare is 12% under it. We do not call a drop notable until 20%, so this is an ordinary price for the route rather than a reason to hurry.
What is the cheapest month to fly from Chicago to Istanbul?
Across 8 months of cached-fare history, Jan comes out cheapest on this route. The best months to actually be in Istanbul are Apr–May · Sep–Oct — when those overlap, that's your window.
How far in advance should I book CHI → Istanbul?
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 8 months of cached fares, Jan 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 Istanbul?
The current cheapest fares involve a connection, ticketed under SAS. 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 Istanbul?
Lock the flight first — then compare stays for 17–31 Jan '27 · 14 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → IST drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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