$35 Cheap flight deals from Chicago (CHI) to Southwest (DEN)
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This Weekend's Flight Deals from Chicago to Southwest
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $35 One Way, $90 Round Trip from Chicago to Southwest
Prices starting at $90 for return flights and $35 for one-way flights to Southwest were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Southwest economy flight packages
Discovery Lodge
May 14 - May 17
Chicago (ORD) to Denver (DEN)
Denver (DEN) to Chicago (ORD)
Reviewed on Oct 7, 2025
Hyatt Regency Denver at Colorado Convention Center
May 22 - May 25
Chicago (MDW) to Denver (DEN)
Reviewed on Jan 27, 2026
The Armstrong Hotel
May 14 - May 17
Chicago (ORD) to Denver (DEN)
Denver (DEN) to Chicago (ORD)
Reviewed on Nov 4, 2025
More About Flying To Southwest from Chicago
Route Information for Flights from Chicago to Southwest
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | DEN |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Southwest
Orbitz combines guaranteed low prices with cutting-edge mobile tools for travel from Chicago to Southwest to give you a travel experience that is second to none.
Bargain Travel at Your Fingertips
Orbitz provides the cheapest fares from Chicago to Southwest. When reserving your flight you can mix and match a range of low cost airlines for you departing and returning domestic or international flights. This way you can travel on a budget while selecting the flights that suit your schedule.
Modern Tools for Fast-Paced Travel
Orbitz makes use of the latest technology to ensure that you are always kept up-to-date on the status of your Chicago to Southwest flights. Through easy-to-use mobile Android and iPhone apps you can book low cost flights from Chicago to Southwest and choose a range of cheap hotels to stay in.
Enjoy Stress-Free Travel with Flight Alerts
Once you have booked your flights from Chicago to Southwest on Orbitz you will always be kept informed of any changes to your flight. When you opt into Orbitz’s free email and SMS alerts on your Chicago to Southwest flights you can ask Orbitz to send the flight details to up to 6 other contacts, so keeping your family and business team informed is a cinch.
Frequent Flyer Program
For loyal Orbitz customers who fly from Chicago to Southwest the chance to join our frequent flyer program is an added bonus. Simply log-on to your online account and input your frequent flyer number for future flights.
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.