Category: Chicago

American Airlines has round-trip flights from Houston (IAH) to Chicago (ORD) for $97, NONSTOP.  August to December. Origin/Destination reversible.

Note: Carry-on bag is allowed for free on American Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat 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 $97 r/t – American

Airfare Deals American Airlines Bookable Deals Chicago Oneworld

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