Category: Chicago

Southwest has round-trip flights from Houston (HOU) to Los Angeles, Fort Lauderdale, Chicago, Orlando, or Baltimore  (LAX, FLL, MDW, MCO, BWI) for $98-$122, NONSTOP. $49-$61 each-way. Flights vary depending on destination, between October and mid-December. Origin/Destination reversible. No Holidays.

Note: Los Angeles is the most expensive of this group; $109-$122.

Note: We believe this sale ends today.

Note: You can save an additional $150 if you book your Flight+Hotel together as a package on Southwest Vacations and use the 150DOM19 coupon-code. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Hotels.com.

Read More Nonstop Flights: Houston to/from Los Angeles, Fort Lauderdale, Chicago, Orlando, or Baltimore $98-$122 r/t – Southwest

Airfare Deals Baltimore Bookable Deals Chicago Fort Lauderdale Los Angeles Orlando Southwest Airlines

American Airlines has round-trip flights from Houston (IAH) to Chicago (ORD) for $97, NONSTOP. Flights October to April. Mostly on Tuesdays, Wednesdays, or Saturdays. Extended Weekends (SAT-TUE) available. 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.

Read More Nonstop Flights: Houston to/from Chicago $97 r/t – American

Airfare Deals American Airlines Bookable Deals Chicago Oneworld

American Airlines has round-trip flights from Houston (IAH) to Miami, Los Angeles, or Chicago (MIA/LAX/ORD) for $97-$131, NONSTOP. Flights vary for each destination, but most are between August to March. No Friday departures. Extended weekends available. 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: These destinations are usually priced within the $97-$139 price range for flights a few months out that aren’t the weekend.

Read More Nonstop Flights: Houston to/from Miami ($109), Los Angeles ($131), or Chicago ($97) r/t – American

Airfare Deals American Airlines Bookable Deals Chicago Los Angeles Miami Oneworld

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 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 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