Category: Chicago

Southwest has round-trip flights from Houston (HOU) to Chicago (MDW) starting at $104, NONSTOP. $52 each-way. Flights from August to October. 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.

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.

Note: You can save an additional $100 if you book your Flight+Hotel together as a package on Southwest Vacations and use the DOM100 coupon-code.

Read More Nonstop Flights: Houston to/from Chicago $104 r/t – Southwest

Airfare Deals Bookable Deals Chicago Southwest Airlines

American Airlines has round-trip flights from Houston (HOU/IAH) to Chicago (ORD) for $101, NONSTOP. $50 each-way. Flights midweek, January to July. No weekends. Origin/Destination reversible.

Note: Fare allows for a free carry-on bag, but a checked bag will have a fee. Seats are assigned randomly at the gate.

Note: Spirit may be matching with fee encumbered fares. Avoid those unless you have a way to get around carry-on bag fees, seat selection fees, and various other fees.

Read More Nonstop Flights: Houston to/from Chicago $101 r/t – American

Airfare Deals American Airlines Chicago Oneworld

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

Airfare Deals Chicago Southwest Airlines

Airfare Deals American Airlines Chicago Oneworld

[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

Airfare Deals Chicago Southwest Airlines

[05/11/2018 @ 11:21 AM] Fewer dates available now. Mostly in September.

Southwest has round-trip flights from Houston (HOU) to Chicago or Atlanta (MDW/ATL) starting at $100, NONSTOP. $50-$55 each-way. Flights from June to September, mostly on Tuesdays, Wednesdays and Saturdays. Weekends available in August and September. Origin/Destination reversible.

Note: United and AA tend to match Southwest fares with inferior “Basic Economy” fares that have bag fees and other various restrictions. Southwest doesn’t charge a change fee or a cancellation fee and allows for 2 checked bags for free.

Note: You can save an additional $100 if you purchase your Flight+Hotel together as a package on Southwest Vacations and use the GETAWAY coupon code.

Read More Nonstop Flights: Houston to/from Chicago / Atlanta $100-$110 r/t – Southwest

Airfare Deals Atlanta Chicago Denver Southwest Airlines

Southwest has round-trip flights from Houston (HOU) to Chicago or Atlanta (MDW/ATL) starting at $102, NONSTOP. $51 each-way. Flights in April and May, mostly on Tuesdays, Wednesdays and Saturdays. Other days of the week are available to a lesser extent. Origin/Destination reversible.

Note: Southwest doesn’t charge a change fee or a cancellation fee and allows for 2 checked bags for free.

Read More Nonstop Flights: Houston to/from Chicago / Atlanta $102-$106 r/t – Southwest

Airfare Deals Atlanta Chicago Denver Southwest Airlines

Airfare Deals Atlanta Chicago Southwest Airlines

[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

Airfare Deals Chicago Southwest Airlines