Open interactive map →Cheap flights from Houston to Chicago
Fares on the Houston to Chicago route are tracked month by month. The lowest observed price is €85. Tracked fares on this route include at least one stop. The calendar below lists the months SkyHopp has fares for - not enough months yet to name a cheapest month.
A price calendar on this page lists tracked months as they fill in. Tracked fares on this route include at least one stop. If you are open on destination, use the interactive map from Houston to compare Chicago against nearby alternatives.
Flying the other way? Cheap flights from Chicago to Houston.
One-way fares
From €85
Cheapest tracked fare
Return fares
From €133
Tracked return fares (out 20 Nov 2026, back 23 Nov 2026)
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Get an email when Houston to Chicago fares are at or below your target price. The email includes the fare.
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Cheapest month to fly
- November 2026€851 stopCheapest
SkyHopp has tracked fares for this route in November at around €85. That is the only month with data so far, so it is too early to name a cheapest month.
Cheapest fare last seen 23 October 2026.
Entry requirements for United States
EU passportESTA required (visa-waiver)
US passportN/A (domestic)
Requirements vary by nationality and change without notice. Check requirements for your nationality →
About Chicago
Chicago is the great American city that the coasts overlook - a dense, architecturally extraordinary lakefront city with world-class museums, deep-dish pizza, and jazz and blues venues that trace the music's northern migration. O'Hare (ORD) and Midway (MDW) together give the city one of the world's widest airport choices.
Alternative routes
Other ways to reach Chicago
Frequently asked questions
How much does a flight from Houston to Chicago cost?
The cheapest tracked fare from Houston to Chicago is €85. The month-by-month price calendar on this page lists the months SkyHopp has fares for. A tracked return fare on this pair is currently from €133. Fares are refreshed as our flight partners publish new availability.
Are there direct flights from Houston to Chicago?
SkyHopp has not observed a non-stop fare from Houston to Chicago in the current dataset. Tracked fares on this pair include at least one stop. Schedules change - check the booking site for a full breakdown by stop count on your dates.
When is the cheapest time to fly from Houston to Chicago?
SkyHopp does not yet have enough months of fares on this route to name a cheapest month. The calendar above lists the months that already have data. Set a price alert on this page to watch the fare.