Cheap flights from Houston to Chicago
The cheapest round trip from Houston to Chicago that travelers found recently is $244 with a carry-on: a $134 fare on Frontier plus about $110 for a carry-on both ways. It leaves Mon, Nov 23 and comes back Tue, Nov 24.
Live prices for Mon, Nov 23 to Tue, Nov 24
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Mon, Nov 23 | Tue, Nov 24 | Frontier | IAH → ORD | Nonstop | $134 | +$110 | $244 | Live price |
| Wed, Dec 16 | Tue, Dec 22 | Frontier | IAH → ORD | 1 stop | $163 | +$110 | $273 | Live price |
| Tue, Dec 15 | Tue, Dec 22 | Frontier | IAH → ORD | 1 stop | $167 | +$110 | $277 | Live price |
| Tue, Dec 15 | Mon, Dec 21 | Frontier | IAH → ORD | 1 stop | $178 | +$110 | $288 | Live price |
| Wed, Dec 16 | Mon, Dec 21 | Frontier | IAH → ORD | 1 stop | $178 | +$110 | $288 | Live price |
| Tue, Nov 24 | Sat, Nov 28 | Frontier | IAH → MDW | 1 stop | $202 | +$110 | $312 | Live price |
| Mon, Nov 23 | Sat, Nov 28 | Frontier | IAH → ORD | Nonstop | $208 | +$110 | $318 | Live price |
| Thu, Dec 17 | Wed, Dec 23 | Frontier | IAH → MDW | 1 stop | $215 | +$110 | $325 | Live price |
| Fri, Oct 16 | Mon, Oct 19 | American Airlines | IAH → ORD | Nonstop | $332 | Included | $332 | Live price |
| Thu, Oct 22 | Mon, Oct 26 | American Airlines | IAH → ORD | Nonstop | $332 | Included | $332 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Fri, Oct 16 to Mon, Oct 19, 3 nights | $332 | Live price |
| November 2026 | Mon, Nov 23 to Tue, Nov 24, 1 night | $244 | Live price |
| December 2026 | Wed, Dec 16 to Tue, Dec 22, 6 nights | $273 | Live price |
Bag fees on this route
What the airlines flying Houston to Chicago usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| American Airlines | Included | $40 |
| Frontier | $55 | $50 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
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