Southwest Cheap Flights From Chicago - (2023)

Emergency And Bereavement Flights

Southwest may add more Cincinnati flights

Buy your emergency Southwest flight with Alternative Airlines. If you are needing to buy a last-minute flight for a funeral or a family emergency, then Alternative Airlines will help you through this stressful process. See all information on flying in an emergency or information on bereavement flights with Alternative Airlines.

Southwest Airlines: Service On Board In

Satellite-based WiFi is available for WiFi-enabled devices and costs $8 a day per device. Devices should be fully charged before boarding the plane, because outlets are not available on the flight. WiFi network content is filtered. Southwests Inflight Entertainment Portal offers flyers a flight tracker, arrival and connecting gate information, games and access to the Southwest website. There is no charge for TV and there is live TV channels and on-demand episodes. Movies cost $5 per move per device and can continue to be viewed if you have a connecting flight. Movies cannot be downloaded to devices. A combination of classic movies, new releases and childrens movies are available. You can also download messaging apps, such as WhatsApp and Viber for $2 a day so you can stay in contact with friends and family who are using the same apps. Messaging is included in the purchase of full access WiFi.

Cheap Flights From Chicago Midway

Flights from Chicago Midway Airport

Want to know how to find seriously cheap flights from Chicago Midway Airport? Try searching on Skyscanner, the internets most comprehensive, advanced travel search engine. Skyscanners award-winning search engine technology ranks consistently as the internets number one best option for finding low fares and last minute flights from Chicago Midway Airport. With Skyscanner, you can be sure that the price youre paying on travel is the lowest possible fare to be found.

To start a search on Skyscanner, visit the search page and type in or select your travel details. For an even more enhanced search performance, read on to find out more about Skyscanners useful tools and features that can help you save even more on your airfare.

Skyscanners Hot Fares from Chicago Midway Airport

Take a look at some recent hot fares weve found using Skyscanner to search for flights from Chicago Midway Airport. To find deals like these, make sure youre using our Skyscanner super saver tools and features to enhance your next search.

  • $237 flights from Chicago Midway Airport to Las Vegas, on Delta Airlines
  • Flights from Chicago Midway Airport to Houston, only $70 each way on Southwest Airlines
  • Just $242 roundtrip on flights from Chicago Midway Airport to Los Angeles on Delta Airlines
  • Flights from Chicago Midway Airport to Traverse City, MI, just $326 on Delta Airlines

Skyscanners Last Minute Flight Finds from Chicago Midway Airport

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Looking For Low Fares Consider Other Airports

Cant find low airfares out of OHare or Midway? For cheap flights, consider expanding your flight search to other area airports.

General Mitchell International Airport in Milwaukee is serviced by more than a dozen airlines . You may be able to find cheap flights to Atlanta, Dallas-Fort Worth, Denver, Phoenix and other destinations.

Allegiant Air and Apple Vacations flights operated by Frontier Airlines fly out of Chicago Rockford International Airport , which is located 68 miles northwest of Chicago in Rockford, Ill. Top destinations include Phoenix, Las Vegas, Orlando, St. Petersburg and Denver.

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Southwest Cheap Flights From Chicago - (1)

In announcing O’Hare service, Southwest said the airline would operate 20 daily flights out of the airport and that one-way prices would begin at $39.

“We’re growing the reach of Southwest as we add more destinations across the United States while bringing our warm Hospitality and iconic Customer Service to more people than ever before,” Andrew Watterson, Southwest Airlines Chief Commercial Officer and Executive Vice President, said in a statement at the time.

Chicago is one of the strongest and most competitive airport markets in the world, and we are always eager to work with our existing airlines and new entrants on enhancing the service they offer to travelers,” the Chicago Department of Aviation said in a statement following the announcement. “This is a vote of confidence in our city and in OHare, and were excited to build on 35 years of partnership with Southwest Airlines.

The Chicago expansion comes as the company also announced plans to return to Houston’s George Bush Intercontinental Airport.

“Southwest owes decades of success to our employees and customers who have supported our business in Chicago and Houston,” Southwest Airlines CEO Gary Kelly said in a release. “Today’s announcement furthers our commitment to both cities as we add service to share Southwest’s value and Hospitality with more leisure and business travelers.”

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Featured Chicago To Las Vegas Flight + Hotel Deals

  • Las Vegas

    Check out the deals at the Luxor for even more savings!

    Features of this hotel include:

  • Feel young, sophisticated, stylish, and energetic at LAX Nightclub.
  • Laugh til you hurt with Carrot Top the award-winning comedian.
  • Enjoy an array of services from massages to manicures at Nurture Spa.
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    Features of this hotel include:

  • Be wowed by the incredible impersonations and ventriloquism of Terry Fator.
  • Immerse in a different type of networking and interact with the dolphins.
  • Have a hoot with the funniest comedians at Aces of Comedy.
  • The Southwest Travel Experience

    At Southwest, we know it takes more than great deals on Fort Lauderdale airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago to Fort Lauderdale the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to Fort Lauderdale-Hollywood International Airport.

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    Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Fort Lauderdale, know that you wont be surprised at checkout. Low fares and no hidden fees. That’s Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? from us. Book your flight today and know that you’ll earn Rapid Rewards® points when you fly.

    1First and second checked bags. Weight and size limits apply.

    2Fare difference may apply.

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    Find Out What’s Happening In Chicagowith Free Real

    • Fort Meyers, Florida, starting at $154
    • New Orleans, starting at $163
    • New York/Newark, NJ, starting at $95
    • New York , starting at $91
    • San Antonio, starting at $143
    • San Francisco, starting at $154
    • Tampa, Florida, starting at $140

    Seattle, starting at $181

    The low fares apply to continental U.S. travel from Sept. 24 to March 4, 2020, in most areas. Exceptions are John Wayne Airport in Santa Ana, California, where travel must be completed from Jan. 7March 4, 2020 inter-island travel in Hawaii and travel to and from Puerto Rico. Fares do not apply to continental U.S. travel to and from the Hawaiian Islands.

    Flash Sale: Southwest Airlines Has $39 Flights But Only For 3

    Southwest adds cheap Florida flight from CVG

    Southwest Airlines is well-known for its $39 one-way flight sales, and just like the previous ones, the airline is back with their winter sale.

    The sale, which started this week, will run until Thursday Nov. 11 at 11:59pm Central Standard Time. Keep in mind that the $39 is just a starting price point, and most one-way fares with be $68.

    This is perfect for anyone looking for a cheap way to get home early for the holidays or for a quick escape this season. Of course, there are some restrictions and blackout dates associated with this Southwest sale.

    Tickets must be purchased for travel that is at least 21-days in advance. You must also travel on Tuesday or Wednesday only. According to the airlines website, routes included are to the continental U.S., continental U.S. to/from Hawaii, and interisland Hawaii travel valid December 1 through December 15, 2021, and January 5 through March 9, 2022. Travel to/from San Juan, Puerto Rico valid December 1 through December 9, 2021, and January 10 through March 9, 2022. International travel valid December 1 through December 15, 2021, and January 5 through March 9, 2022.

    You can view all rules and restrictions for the sale here.

    Weve checked out the sale list and wanted to let you know a few mention-worthy routes.

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    You can fly from New York to Chicago for $68, Los Angeles to Honolulu, Hawaii for only $99 one-way, and even Charlotte, NC to New Orleans for only $84.

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    Southwest Airlines Eyes New Routes For 2021

    Southwest Airlines announced last month that it will be adding an additional route between Kahului , Hawaii, and Long Beach, Calif. From March, Southwest Airlines will also commence an additional six new routes from Long Beach including Chicago , Dallas , Honolulu , Houston , Kahului , Reno/Tahoe, and St. Louis. This news follows a difficult year for the travel industry, due to the Coronavirus pandemic, and suggests that, despite this, Southwest still sees continued growth in the future.

    3 September 2020

    Looking To Book Southwest Airlines Flight Tickets

    Alternative Airlines is an online flight search and booking site, which offers competitive Southwest Airlines airfare prices. We make it easy to pay the way you want, whether that is using PayPal or splitting the cost with Sezzle, Affirm, Quadpay, or one of our other payment plan options. Make your flight reservation with no need to pay the full cost of your Southwest Airlines flights today.

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    Southwest Airlines: How To Check In Seating Assignment Leg Room And Other Fees

    Online check-in at is available for Southwest passengers. You can also check-in at the self-service kiosk. Check-in can be done beginning 24 hours before departure. A government ID is needed for checking luggage. This can be shown at the Ticket Counter or Skycap Podium. Both the boarding pass and government-issued ID should be presented at the security line. Go directly to the security line if you do not have luggage to check-in.

    You will be assigned a boarding position of A, B, or C and a number between 1 and 60 when you check in. This letter-number combination can be found on your boarding pass. Business select partners are in group A. Rapid Rewards tier members and families with children aged 6 and under are also in group A. Group B will go next, and C will go last. Passengers should plan on being at the gate 30 minutes before the departure time. Boarding passes will be checked at the gate 10 minutes prior to departure.

    Seniors, 65 and older, qualify for senior fares and can make reservations for domestic and international flights online or by contacting a Southwest Airlines Customer Service Representative or travel agent. If you do not meet the above age requirement, there are other discounted fares which may be available to you. A Southwest Airlines representative can provide you with more information about these offers.

    Take A Break From Chicagos Winter Weather

    Southwest Cheap Flights From Chicago - (2)

    During winter months, warm-weather destinations arenot surprisinglypopular with Chicagoans.

    Many families head to Orlando to visit Walt Disney World and other area amusement parks. Beach destinations such as Cancun, Fort Myers, Honolulu and San Juan are favorites of those who want to relax, soak up the suns rays or partake in outdoor sports such as fishing and surfing. Phoenix is also a hot destination, particularly among golfers.

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    How Can I Find Cheap Flights From Chicago To Fort Myers Southwest Florida Reg

    Be flexible and open to travelling during off-peak times like mid-week and later in the evenings or early mornings. Flights between Chicago and Fort Myers Southwest Florida Reg are likely to be cheaper during these times, as the cheapest flight fares are usually found outside of peak times. You can read more about finding cheap flights in our dedicated guide.

    Chicago To Las Vegas Deals

    Enjoy these great Chicago to Las Vegas vacation deals. Book your Las Vegas vacation package with flights from Midway with Southwest Vacations® and you’ll be on your way to a fun-filled vacation. We’ve worked with our partners to secure amazing deals to ensure everyone is a winner! Book one of our Las Vegas vacation deals from Chicago today, before they are all gone.

    Las Vegas fun fact: More than 38.9 million people visit Las Vegas each year, so book your vacation to Las Vegas today, and experience the thrill of Vegas that so many people enjoy.

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    When Is The Best Time To Book Flights From Chicago O’hare International To Fort Myers Southwest Florida Reg

    The best times to book flights are typically on Tuesday or Wednesday. Avoid booking flights from Chicago O’Hare International to Fort Myers Southwest Florida Reg on Fridays and Saturdays, as flight prices tend to fluctuate during those days. You can read more about the best time to book in our dedicated Best Time to Book guide.

    Why Book Las Vegas From Chicago With Southwest Vacations

    Southwest Airlines flying into CVG

    Here are just some of the benefits youll experience when booking your Las Vegas Vacations package with Southwest Vacations:

    • Southwest Vacations is the official leisure vacation package provider for Southwest Airlines. When you book with Southwest Vacations you also experience the benefits of Southwest Airlines.
    • Your first and second bags fly free.
    • If you need assistance before, during, or after your travel we are there to help 24-hours a day.
    • If you find the price of your exact Southwest Vacations package is lower than the price you paid well issue a travel credit for the difference, all you need to do is just contact us.
    • Earn Rapid Rewards Points on the flight portion for each Southwest Airlines® air-inclusive vacation itinerary booked through
    • If you realize you need to make a change to your travel dates, time, or hotel, Southwest Vacations does not charge any fees or penalties to modify your vacation package.
    • Be the first to know about the latest sales and promotions when you sign up to receive the Southwest Vacations e-mail.
    • Past Customers also receive exclusive offers throughout the year.

    Not finding what you are looking for? View all Las Vegas deals

    First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag.

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    Essential Travel Information: Chicago O’hare International To Fort Myers Southwest Florida Reg

    Our travel information panel above gives useful information about:

    • The distance between Chicago O’Hare International and Fort Myers Southwest Florida Reg
    • The time it takes to fly to Fort Myers Southwest Florida Reg from Chicago O’Hare International
    • The airlines with the cheapest flights from Chicago O’Hare International to Fort Myers Southwest Florida Reg
    • The airlines which fly direct to Fort Myers Southwest Florida Reg from Chicago O’Hare International.


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