$99 Economy Roundtrip to San Diego (MDW-SAN) in Feb from Chicago

February departures from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) combine cold-weather precautions at origin with mild-weather planning for arrival. This monthly route guide highlights weather considerations, packing, transport options, likely airlines and fares, and nearby destinations you can reach from both airports.

Departing from Chicago (MDW) FAQs

In February, check-in at Chicago Midway International Airport (MDW) typically requires arriving 90–120 minutes before a domestic flight due to winter weather contingency and holiday weekend travel like Presidents' Day. TSA wait times vary by time of day; early mornings and late evenings tend to be shorter. Use TSA PreCheck or arrive earlier on peak travel dates to avoid stress.

February brings winter storms and lake-effect snow to the Chicago area that can cause delays or cancellations at Chicago Midway International Airport (MDW). Airlines typically publish flexible rebooking policies during major winter storms; monitor your airline notifications and the FAA's operations alerts. Plan extra travel time to and from the airport and consider travel insurance for key trips.

Popular options include the CTA Orange Line train for direct downtown access, rideshare services like Uber/Lyft, airport shuttles, and taxis. In February, allow extra time for road delays from snow removal; CTA runs on schedule but check for weather advisories. For budget travel, the Orange Line stays the most reliable and cost-effective option from downtown Chicago.

Yes — in February you can often find nonstop service on carriers such as Southwest Airlines between Chicago Midway International Airport (MDW) and San Diego International Airport (SAN). Frequency varies by airline and day of week, with more direct options on weekends and holidays. Book early to lock in direct flights, especially around President's Day travel windows.

Pack warm layers and a compact, insulated coat in checked luggage if you don't want it in the cabin; expect airlines' standard checked bag fees unless you have status or credit card benefits. Salt and wet snow can affect clothing — use protective garment bags for suits or delicate items. Keep essential items and a change of clothes in carry-on luggage in case of delays or lost bags.

For low fares in February, search midweek departures (Tues–Thurs), set fare alerts, and book 3–6 weeks ahead of travel. Use flexible date searches and check Southwest's sale periods for MDW–SAN routes; consider connecting flights via Phoenix or Denver if direct fares are high. Sign up for airline newsletters and use incognito mode to compare prices without dynamic fare increases.

Arriving at San Diego International Airport (SAN) in February offers mild weather, fewer crowds, and access to coastal attractions like La Jolla and Coronado. This monthly arrival guide helps visitors from Chicago Midway International Airport (MDW) plan transport, day trips, and seasonal activities so they can maximize time in Southern California.

Arriving at San Diego (SAN) FAQs

San Diego International Airport (SAN) is a short 4–8 minute drive to the Gaslamp Quarter and downtown San Diego by taxi or rideshare. The airport shuttles and public transit options (MTS trolley and trolleys + buses) connect to nearby neighborhoods; check weekend and holiday schedules in February for possible adjustments. February weather is mild, making short transfers pleasant, but always confirm timing for evening events.

February is ideal for visiting La Jolla's coast, Coronado's beaches, Carlsbad's flower fields (season-dependent), and nearby Temecula wine country for day trips. Expect cooler mornings and comfortable afternoons — pack a light jacket for coastal breezes. These destinations are easily accessible from San Diego International Airport (SAN) by rental car or shuttle services.

February often features San Diego Restaurant Week (late January to early February) and Chinese New Year celebrations in local neighborhoods like the Convoy District. February also brings lesser crowds to popular spots like Balboa Park and the USS Midway Museum, making sightseeing more relaxed. Check local event calendars for exact dates and book reservations ahead for restaurant week.

Yes — SAN has multiple rental car counters and nearby consolidated rental facilities with shuttle service; February generally has good availability but weekends and special events can increase demand. Reserve in advance for best rates and check for off-airport shuttle times. Consider compact cars for easier parking in urban areas like La Jolla and downtown.

San Diego in February is typically mild with daytime highs in the mid-60s°F (around 18°C) and cooler evenings; pack layers, a light rain jacket, and comfortable shoes for walking. Travelers coming from Chicago Midway International Airport (MDW) should plan to transition from heavy winter gear to lighter coastal clothing — keep an outer layer handy for early mornings or ocean breezes. Sunscreen is useful even in winter.

1.0.2512.03

February Events & Festivals Near SAN and MDW — What to See During Your MDW→SAN Trip

February offers a variety of events for travelers on the MDW→SAN route. San Diego often hosts San Diego Restaurant Week (late January to early February), cultural celebrations like Chinese New Year in local hubs, and low-season museum and harbor activities that are easier to enjoy without crowds. On the Chicago side, Presidents' Day weekend increases airport and road congestion around Chicago Midway International Airport (MDW), so plan ahead if traveling during that long weekend.

Best Time to Fly MDW to SAN — February Insights

For February travel from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN), the best balance of price and convenience is typically midweek (Tuesday–Thursday). Early morning departures can avoid propagated delays from earlier domestic disruptions, while late-night flights sometimes offer lower fares. Avoid Presidents' Day weekend if you want lower prices and quieter airports; otherwise, book midweek for best savings and reliability.

Direct vs Connecting Flights — MDW to SAN in February

Nonstop flights from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) are faster (about 4–4.5 hours) and reduce baggage handling and missed-connection risk — ideal for business trips and short stays. Connecting itineraries (via PHX, DEN, or LAX) can be cheaper, offer more schedule flexibility, and sometimes open up earlier or later departure times, but they add layover time and increase exposure to winter weather disruption in February. Choose nonstop for convenience and reliability; choose a connection to save money if you have a flexible schedule.

Airline Comparison for MDW→SAN in February — Southwest, American, United, Alaska

Southwest Airlines typically offers the most nonstop schedules between Chicago Midway International Airport (MDW) and San Diego International Airport (SAN), making it a top choice for direct travel; its two free checked bags policy is a strong advantage for leisure travelers. American and United may provide competitive connecting options via Phoenix (PHX) or Denver (DEN) with loyalty program benefits for status holders. Alaska Airlines can be a good choice for transcontinental connections via Seattle or LAX with strong premium-cabin service on select flights. Evaluate total trip time, baggage needs, and change/cancellation policies when comparing February fares.

Seasonal Travel Tips for MDW→SAN in February — Packing, Weather & Delays

Pack for a transition: heavy winter gear for your time in Chicago with lighter layers for San Diego. In February, bring a warm coat for departure from Chicago Midway International Airport (MDW) and a light jacket for San Diego cooler evenings. Allow extra time for snow clearing and de-icing at MDW, enroll in TSA PreCheck for faster security lines, and download your airline's app for real-time flight updates and easy rebooking if weather disrupts travel plans. Consider refundable fares or flexible tickets during the winter season.

Flight Time & Schedules — Chicago Midway (MDW) to San Diego (SAN) in February

Typical nonstop flight time from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) ranges from approximately 4 hours to 4 hours 30 minutes depending on winds and routing. In February, airlines often schedule morning and evening nonstops with additional mid-day options on peak travel days; connecting itineraries commonly route through Phoenix (PHX), Denver (DEN), or Los Angeles (LAX) and can add 1–3 hours of total travel time depending on layovers. Check real-time schedules and book preferred departure times early to secure optimal seat choices.

Cheap Flights MDW to SAN in February — Tips & Best Booking Windows

To find cheap flights from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) in February, target a 3–6 week booking window and prioritize Tuesday–Thursday departures. Set multi-airline fare alerts and check Southwest sales regularly, since Southwest frequently operates nonstops between MDW and SAN. Be flexible with travel dates around Presidents' Day, compare connecting itineraries via PHX or DEN for savings, and use incognito browsing or a trusted fare aggregator to avoid dynamic price bumps.

Wed, Feb 4

Roundtrip

Tue, Feb 10

Tue, Feb 3

Roundtrip

Mon, Feb 9

Thu, Feb 5

Roundtrip

Wed, Feb 11

Sun, Feb 1

Roundtrip

Sat, Feb 7

Sat, Feb 7

Roundtrip

Fri, Feb 13

Mon, Feb 2

Roundtrip

Sun, Feb 8

Fri, Feb 6

Roundtrip

Thu, Feb 12

Other Destinations

Flights from Other Cities

Departing from Chicago (MDW) FAQs

What are the typical check-in and security wait times at Chicago Midway International Airport (MDW) in February?

How likely are flight delays or cancellations from MDW to SAN in February due to winter weather?

What ground transport options are best for getting to and from Chicago Midway International Airport (MDW) in February?

Are there direct flights from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) in February?

What are best practices for baggage and winter gear when departing MDW in February?

How can I find cheap February flights from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN)?

Arriving at San Diego (SAN) FAQs

How do I get from San Diego International Airport (SAN) to downtown San Diego or the Gaslamp Quarter in February?

What San Diego neighborhoods or day trips are best to visit in February after arriving at SAN?

Are there any February events or seasonal attractions near San Diego International Airport (SAN)?

Is it easy to rent a car at San Diego International Airport (SAN) in February?

What should travelers know about San Diego weather and clothing when arriving from MDW in February?

February Events & Festivals Near SAN and MDW — What to See During Your MDW→SAN Trip

Best Time to Fly MDW to SAN — February Insights

Direct vs Connecting Flights — MDW to SAN in February

Airline Comparison for MDW→SAN in February — Southwest, American, United, Alaska

Seasonal Travel Tips for MDW→SAN in February — Packing, Weather & Delays

Flight Time & Schedules — Chicago Midway (MDW) to San Diego (SAN) in February

Cheap Flights MDW to SAN in February — Tips & Best Booking Windows

Flight Options & Prices:

Cheap economy Flights: MDW to SAN in February - Route 3

Flight Options & Prices:

Cheap economy Flights: MDW to SAN in February - Route 4

Flight Options & Prices:

Cheap economy Flights: MDW to SAN in February - Route 5

Flight Options & Prices:

Cheap economy Flights: MDW to SAN in February - Route 6

Flight Options & Prices:

Cheap economy Flights: MDW to SAN in February - Route 7

Flight Options & Prices:

Why Choose Economy Class Flights from Chicago (MDW) to San Diego (SAN)?