Category: Chicago

Southwest has round-trip flights from Houston (HOU) to Chicago (MDW) starting at $90, NONSTOP. $45 each-way. Flights from October to February. Origin/Destination reversible.

Note: United, Spirit, and Frontier may have fee encumbered “Basic Economy” fares available for a bit less. Keep in mind that those “cheaper” fares are often more expensive once you factor in bag fees.

Read More Nonstop Flights: Houston to/from Chicago $90 r/t – Southwest

[07/07/2018 @ 1:15 PM] Fare gone. Removing from deal list.

Southwest has round-trip flights from Houston (HOU) to Chicago (MDW) starting at $110, NONSTOP. About $55 each-way. Flights late-July to mid-November. Weekends available. Origin/Destination reversible.

Note: You can save an additional $50-$150 if you book your Flight+Hotel together as a package on Southwest Vacations, and use either the PLANSAVE or FREEDOM coupon-codes.

Read More Nonstop Flights: Houston to/from Chicago $110 r/t – Southwest

[11/10/2017 @ 3:20 PM] Fare gone. Removing from deal list.

Southwest has round-trip flights from Houston (HOU) to Chicago (MDW) starting at $76, NONSTOP. $38 each-way. Flights November 2017 to February 2018. Origin/Destination reversible. Holiday blackouts apply.

Note: United and AA have their inferior “Basic Economy” fares available at this price. Those will only be worth it if you have status or the airline branded credit card that will allow you to check a free bag.

Note: Southwest doesn’t charge a change-fee, so if you already booked this flight, but paid more, you should be able to re-book at the lower price and get the difference paid back to you in the form of a travel-voucher.

Read More Nonstop Flights: Houston to/from Chicago $76 r/t – Southwest