Cheap flights from Houston to Chicago from $97 HOU, IAH → MDW, ORD, RFD

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $127 to $232.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 15-night return fares leaving within 3 days of 22 Dec to compare.

Every date we hold

175 fares on 11 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $180.

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $58 to $197.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other one-way fares leaving within 3 days of 13 Dec to compare.

Every date we hold

4 fares on 4 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $97.

Return

Fares 60 to 89 days before departure were typically 61% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

One-way

Fares 30 to 59 days before departure were typically 38% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

How much is a return flight from Houston to Chicago?

The cheapest return found recently is $211 with Frontier Airlines, 22 Dec to 6 Jan 2027, found 2 days ago. The cheapest return we hold, of any age, is $180 with Frontier Airlines, 2 Dec to 6 Dec, found 7 days ago. The cheapest return fare on each of 11 departure dates is usually $220 to $316.

How much is a one-way flight from Houston to Chicago?

The cheapest one-way found recently is $97 with Frontier Airlines, 13 Dec, found 2 days ago. The cheapest one-way fare on each of 4 departure dates is usually $98 to $159.

What is the cheapest month to fly from Houston to Chicago?

December 2026 is the cheapest month for a return, from $180, 2 Dec to 6 Dec, found 7 days ago. It is the cheapest month for a one-way too, from $97, 13 Dec, found 2 days ago.

How far ahead should I book a flight from Houston to Chicago?

In 49 days of prices between 24 Sept and 11 Nov, return fares 60 to 89 days before departure were typically 61% lower than 0 to 6 days before departure. One-way fares 30 to 59 days before departure were typically 38% lower than 0 to 6 days before departure.

Is there a direct flight from Houston to Chicago?

Yes, the cheapest nonstop return found recently is $361 with Frontier Airlines, 2 Dec to 6 Dec, found 3 days ago. The cheapest nonstop one-way found recently is $158 with Frontier Airlines, 27 Dec, found 5 days ago.

How long is the flight from Houston to Chicago?

The cheapest nonstop one-way found recently, with Frontier Airlines on 27 Dec, takes 2 h 52 min from George Bush Intercontinental Airport (IAH) to O'Hare International Airport (ORD). The cheapest one-way found recently, with Frontier Airlines on 13 Dec, takes 9 h 42 min with 1 stop.

Which airlines have the cheapest flights from Houston to Chicago?

Between 21 Nov and 1 Jul 2027, Frontier Airlines has the cheapest return on 9 of the 11 departure dates we hold, United Airlines on 1 and Southwest Airlines on 1. Between 16 Nov and 29 Jan 2027, Frontier Airlines has the cheapest one-way on 3 of the 4 departure dates we hold, and American Airlines on 1.