Southwest has round-trip flights from Dallas (DAL) Orlando, Fort Lauderdale, or Tampa (MCO, FLL, TPA) for $124-$134, NONSTOP. $62-$67 each-way. Flights mostly from February to May. Origin/Destination reversible. No Holidays. Lots of availability after April 15th.

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 may find additional savings if you book your Flight+Hotel together as a package on Southwest Vacations. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Tripadvisor and Expedia.

Read More Nonstop Flights: Dallas to/from Orlando, Fort Lauderdale, or Tampa $124-$134 r/t – Southwest

Airfare Deals Chicago Southwest

Southwest has round-trip flights from Dallas (DAL) Chicago (MDW) for $98-$106, NONSTOP. $48-$53 each-way. Flights mostly from February to May. Origin/Destination reversible. No Holidays. Sparse availability in March. Lost of availability after April 15th.

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 $150 if you book your Flight+Hotel together as a package on Southwest Vacations and use the US150OFF coupon-code.

Read More Nonstop Flights: Dallas to/from Chicago $98-$106 r/t – Southwest

Airfare Deals Chicago Southwest

American Airlines has round-trip flights from Dallas (DFW) to Chicago (ORD) for $97, NONSTOP. Flights November to April. No Monday departures. No Holidays. Weekends available.

Southwest usually matches this sale.

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.

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

Airfare Deals American Airlines Chicago Oneworld

Southwest has round-trip flights from Dallas (DAL) Chicago (MDW) for $98, NONSTOP. $48 each-way. Flights mostly from January to March. 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 $125 if you book your Flight+Hotel together as a package on Southwest Vacations and use the 125DOM19 coupon-code. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Hotels.com or HotelsCombined.

Read More Nonstop Flights: Dallas to/from Chicago $98 r/t – Southwest

Airfare Deals Chicago Southwest

[06/07/2019 @ 12:20 PM] Still available from last month.

American Airlines has round-trip flights from Dallas (DFW) to Chicago (ORD) for $97, NONSTOP. August to December. Departures on Tuesday, Wednesday, and Saturday.

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: Dallas to Chicago $97 r/t – American

Airfare Deals American Airlines Chicago Oneworld

Southwest has round-trip flights from Dallas (DAL) Las Vegas (LAS) for $90, NONSTOP. $45 each-way. Flights from September to October. Midweek departures with Saturday returns. 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 $60 at MGM Resorts in Las Vegas if you book your Flight+Hotel together as a package on Southwest Vacations and use the 60MGM coupon-code.

Read More Nonstop Flights: Dallas to/from Las Vegas $90 r/t – Southwest

Airfare Deals Chicago Las Vegas Southwest

Southwest has round-trip flights from Dallas (DAL) Chicago (MDW) for $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: Dallas to/from Chicago $104 r/t – Southwest

Airfare Deals Chicago Southwest

American Airlines has round-trip flights from Dallas (DFW) to Chicago (ORD) for $97, NONSTOP. Flights in April, July, August, September, October, November, and December. No Thursday departures. A few 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.

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

Airfare Deals American Airlines Chicago Oneworld

Southwest has round-trip flights from Dallas (DAL) Baltimore (BWI) for $134, NONSTOP. $67 each-way. Flights from January to May. Origin/Destination reversible. No Holidays.

Note: You can save an additional $100 if you purchase your Flight+Hotel together as a package on Southwest Vacations and use the US100OFF coupon-code at checkout.

Read More Nonstop Flights: Dallas to/from Baltimore $134 r/t – Southwest

Airfare Deals Baltimore Chicago Denver Southwest

American Airlines has round-trip flights from Dallas (DFW) to Chicago (ORD) starting at $97, NONSTOP. $49 each-way. Flights in January to June. Friday departures are available for about +$6 more. Origin/Destination reversible.

Note: Cheapest flights are on Tuesdays, Wednesdays and Saturdays.

Note: Carry-on bag is allowed for free, but checked bag will cost about +$30 each way. Seat is assigned randomly, for free at the gate.

Read More Nonstop Flights: Dallas to/from Chicago $97-$103 r/t – American

Airfare Deals American Airlines Chicago Oneworld

Airfare Deals Baltimore Chicago Denver Southwest

Airfare Deals Chicago Denver Southwest

[07/06/2018 @ 11:14 AM] Fare gone. Removing from deal list.

Southwest has round-trip flights from Dallas (DAL) to Chicago or Atlanta (MDW/ATL) starting at $104, NONSTOP. $52 each-way. Chicago flights from August to March. Atlanta flights from August to November. Weekends available. Origin/Destination reversible.

Note: Christmas / New Years is available for Chicago.

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. Coupons expire on 07/09/18.

Read More Nonstop Flights: Dallas to/from Chicago or Atlanta $104-$110 r/t – Southwest

Airfare Deals Atlanta Chicago Southwest

[07/05/2018 @ 3:02 PM CT] Mostly sold out. But you can often find midweek flights for $100 on any given day. Removing from deal list.

American Airlines has round-trip flights from Dallas (DFW) to Chicago (ORD) for $103 with a connection. $51 each-way. Flights Tuesdays, Wednesdays, and Saturdays from mid-August to mid-November. Origin/Destination reversible. Holiday blackouts apply.

Note: This is a “Regular Economy” fare and allows for a carry-on bag and a personal item.

Note: Most Saturday departures are in October and November.

Read More Nonstop Flights: Dallas to/from Chicago $103 r/t – American

Airfare Deals Chicago Oneworld

Southwest has round-trip flights from Dallas (DAL) to Chicago (MDW) or Atlanta (ATL) starting at $92 NONSTOP. $46 each-way. Flights in April. Departs on Tuesdays, Wednesdays, and Saturdays. Origin/Destination reversible.

Note: You can save an additional $100 if you purchase your Flight+Hotel together as a package on Southwest Vacations and use the DOM0318 coupon-code. Coupon expires 03/26/18. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Hotels Combined or Hotels.com.

Read More Nonstop Flights: Dallas to/from Chicago / Atlanta $92-$94 r/t – Southwest

Airfare Deals Atlanta Chicago Southwest

[02/21/2018 @ 10:37 AM] Old post clean-up. Fare gone. Removing from deal list.

Southwest has round-trip flights from Dallas (DAL) to Chicago (MDW), Detroit (DTW), or Pittsburgh (PIT) starting at $82 NONSTOP. $41 each-way. Flights January to early-March. Origin/Destination reversible. Very few Sunday returns. No Holidays.

Note: You can save an additional $125 if you purchase your Flight+Hotel together as a package on Southwest Vacations and apply the SAVE125 coupon code. Package coupon expires today, but the airfare deal should still be around.

Read More Nonstop Flights: Dallas to/from Chicago / Detroit / Pittsburgh $82-$88 r/t – Southwest

Airfare Deals Chicago Detroit Pittsburgh Southwest

Airfare Deals Chicago Oneworld Philadelphia Southwest

[08/17/2017 @ 1:07 AM] Still available. August fares gone. September and later still available.

American Airlines has round-trip flights from Dallas (DFW) to Chicago (ORD) for $98, NONSTOP. $50 each-way. Flights scattered in September and also November to February. Weekends available. Holiday blackouts apply. Origin/Destination reversible.

Read More Nonstop Flights: Dallas to/from Chicago $98 r/t – American

Airfare Deals American Airlines Chicago Oneworld

Airfare Deals American Airlines Chicago Oneworld

Southwest and United have round-trip flights from Dallas (DFW/DAL) to Chicago (ORD/MDW) for $88, NONSTOP. $44 each way. Flights are midweek TUE/WED January to April. Origin/Destination reversible. Expect prices to fluctuate +/- $10.

Note: United only has flights in January and February. Southwest has much better availability.

Read More Nonstop Flights: Dallas to/from Chicago $88 r/t – Southwest / United

Airfare Deals American Airlines Chicago Oneworld Southwest Star Alliance United