Save BIG on Southwest Airlines Flights to Chicago

Cheap Southwest Airlines Flights to Chicago on TravelOblue

Travel smart and save more on your trip to Chicago. With Southwest Airlines's budget-friendly economy class options, you get comfort, flexibility, and excellent service at a low cost. Perfect for value-conscious travelers—book now on TravelOblue!

Want to get the best last-minute deal? Take advantage of our 24/7 customer support at +1-878-255-3131

Types of Travel Classes Available for Booking with Southwest Airlines

Enjoy Hassle-Free Booking of Southwest Airlines cheap flights booking, flexible fares, and top-notch service every step of the way.

Travel Classes

Southwest Airlines booking provides four fare classes catering to different travel needs. Whether you prioritize affordability, flexibility, or premium benefits, there’s a fare for you. Explore the options below to find the best fit for your trip.

Wanna Get Away

Southwest Wanna Get Away is the most affordable fare, offering budget-friendly pricing with essential services. Though non-refundable, cancellations provide travel credits for future flights. Passengers earn 6 Rapid Rewards points per dollar spent. It’s a great choice for travelers looking to save while enjoying Southwest’s signature hospitality.

Wanna Get Away Plus

An upgraded version of Wanna Get Away, this fare offers more flexibility. It includes transferable flight credits and confirmed free same-day changes based on seat availability. Travelers also earn 8 Rapid Rewards points per dollar. Southwest Wanna Get Away Plus is perfect for those who want affordable travel with added benefits.

Anytime

Designed for flexibility, Southwest Anytime fare is fully refundable, making it ideal for unpredictable schedules. It includes EarlyBird Check-In and access to priority lanes where available. Passengers earn 10 Rapid Rewards points per dollar. This premium economy fare is great for business travelers or those needing last-minute airlines ticket changes.

Business Select

Southwest’s Business class flight fare offers priority boarding (A1-A15), a complimentary premium drink on flights over 176 miles, and free in-flight internet. It’s fully refundable and provides the highest reward points, earning 12 Rapid Rewards points per dollar. Southwest Business Select is the best option for travelers who want convenience and added comfort.

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Find the Best Flight Deals to Chicago

Ready for a Chicago getaway or a round trip back? Compare fares across top airlines and unlock exclusive offers on one-way and round-trip flights.

Airports in Chicago

CHI - CHI - Chicago All Airports, Illinois, United States
GYY - Gary Regional
MDW - Midway
ORD - Ohare International

How can I save on Southwest Airlines Bookings to Chicago?

Plan ahead and save on Southwest Airlines bookings with limited-time offers and unpublished phone-only fares.

1. Explore Nearby Cities

For better savings, check flights to or from nearby cities. Southwest Airlines often offers lower fares through alternate airports—especially during off-peak travel months.

2. Travel on Flexible Dates

Moving your departure date forward or back by a day can reveal hidden deals on Southwest Airlines flights. Stay flexible and save more.

3. Use Seasonal Trends to Your Advantage

October to March is considered a low season for travel to Chicago, which often means cheaper Southwest Airlines fares. Book during these months to get the best value.

4. Know the Southwest Airlines Refund Policy

Southwest Airlines offers flexible booking options on select fares. Check the latest Southwest Airlines refund policy to understand your rights if plans change or cancellations become necessary.

5. Separate Your Bookings for Better Deals

Booking with multiple airlines instead of one round-trip provider can lead to significant savings. It’s a great way to compare fares and customize your journey.

Southwest Airlines Flights to Chicago - FAQ

You can fly to 4 major airports: CHI - Chicago All Airports, Illinois, United States - CHI, Gary Regional - GYY, Midway - MDW, and Ohare International - ORD. Choose round trip flights to Chicago based on flight deals, proximity, and airline availability.

Yes, Southwest Airlines also operates flights to cities like Cancun, Las Vegas, Orlando, Denver, Montego Bay, Puerto Vallarta, , in addition to many other international destinations.

Yes! On TravelOblue, just enter your trip details and select “Economy or Premium Economy.” You’ll find great Southwest Airlines deals to Chicago, with filters to help you compare fares and routes. For expert assistance or special rates, call us at +1-878-255-3131.

You can manage your booking directly through the airline’s website using the booking reference or contact our customer support for assistance.

Refunds and cancellations depend on the airline’s policy. Please review the fare rules when booking or contact us for guidance on your specific ticket.

We use secure encryption technology to protect your payment and personal information, ensuring a safe booking experience.

No, we prioritize transparency. You see the price you pay, with no hidden fees or unexpected costs.

Absolutely! TravelOblue offers excellent deals on last-minute flights, helping spontaneous travelers secure the best rates quickly.

Use our search engine to compare airline deals across multiple platforms. Apply filters like flexible dates, stops, and preferred airlines to discover the most affordable options.

If you have any questions or need assistance with your travel arrangements or best airline deals, you can reach our customer support team 24/7 at +1-878-255-3131.

Yes, you can change or cancel your Southwest Airlines flight to Chicago, but the flexibility depends on your fare type. Most non-refundable tickets allow changes for a fee or fare difference, while fully refundable fares offer more freedom. Always review your fare rules before making changes, and for hassle-free modifications, call us at +1-878-255-3131 for expert assistance.