Cheap Flights from San Francisco to Chicago
Find budget flights starting at $382 (30% below average)
Lowest Price
$382
Basic economy fare
Average Price
$545
Standard fare
Cheapest Month
February
Best time to fly
Book Ahead
6-8
Weeks in advance
How to Find Cheap San Francisco to Chicago Flights
Looking for cheap flights from San Francisco to Chicago? You've come to the right place. With smart booking strategies and flexibility, you can save up to $164 on this route, with fares starting as low as $382 for economy class tickets.
Budget Airlines on This Route
Several low-cost carriers operate between SFO and ORD, offering no-frills service at competitive prices. While these airlines may charge extra for baggage, seat selection, and onboard amenities, their base fares are often 30-50% lower than traditional carriers.
Best Times for Cheap Flights
The cheapest flights from San Francisco to Chicago are typically found during off-peak travel periods. Avoid major holidays, summer vacation months, and popular event dates in either city. Tuesday and Wednesday departures often offer the lowest fares, while Friday and Sunday flights command premium prices.
Money-Saving Booking Tips
- Book at least 6-8 weeks in advance for the best deals
- Be flexible with your travel dates - use our fare calendar to find the cheapest days
- Consider alternative airports near San Francisco or Chicago
- Sign up for fare alerts to catch flash sales and error fares
- Clear your cookies or use incognito mode when searching for flights
- Compare one-way tickets vs. round-trip fares - sometimes two one-ways are cheaper
Hidden Fees to Watch For
When booking cheap flights, be aware of additional fees that can add up quickly. Budget airlines often charge for checked baggage ($25-50), carry-on bags ($35-65), seat selection ($10-75), and even printing boarding passes at the airport. Factor these costs into your total travel budget when comparing fares.
Alternative Routes to Save Money
Sometimes booking connecting flights can save you money on the San Francisco to Chicago route. Consider flights with one stop in major hub cities, though be sure to allow adequate connection time. Multi-city itineraries or open-jaw tickets might also offer savings for flexible travelers.
Price Trends & Best Booking Times
Cheapest: February
Book for lowest fares
Best Days: Tue-Wed
Fly midweek to save
Book: 6-8 weeks ahead
Optimal booking window
Budget Airlines on This Route
These low-cost carriers offer the cheapest base fares between SFO and ORD:
Southwest
From $358
Frontier
From $415
Spirit
From $392
Allegiant
From $409
Budget Airline Fees to Consider:
- Carry-on bags: $35-65
- Checked bags: $25-50
- Seat selection: $10-75
- Priority boarding: $15-30
Money-Saving Flight Hacks
Be Flexible with Dates
Use flexible date search to find the cheapest days. Flying one day earlier or later can save you $55-$109.
Book One-Way Tickets
Sometimes two one-way tickets are cheaper than round-trip, especially when mixing airlines.
Red-Eye & Early Flights
Flights departing very early (before 6 AM) or late night often cost 20-30% less.
Clear Cookies & Use Incognito
Airlines may show higher prices on repeat searches. Use private browsing for best rates.
Alternative Money-Saving Options
Consider Nearby Airports
Flying from alternative airports can offer significant savings:
Near San Francisco:
Check airports within 100 miles for better deals
Near Chicago:
Consider secondary airports for budget options
Multi-City & Stopover Tricks
Sometimes booking SFO → Hub → ORD as separate tickets can save money. Popular stopovers include major hubs where you might even explore another city!
When to Book Cheap San Francisco to Chicago Flights
Best Booking Times
- Tuesday at 3 PM ET (airline sales)
- 21-60 days before departure
- Off-season months for destination
Avoid These Times
- Major holidays & school breaks
- Less than 14 days before travel
- Peak summer months (June-August)
Cheap Flights FAQ
What's the cheapest day to fly from San Francisco to Chicago?
Tuesday and Wednesday departures typically offer the lowest fares, with savings of $82-$136 compared to weekend flights. Early morning and late night flights also tend to be cheaper.
How far in advance should I book for the cheapest flights?
For SFO to ORD, book domestic flights 6-8 weeks in advance for the best deals. Prices typically increase sharply within 14 days of departure.
Are budget airlines really cheaper after all fees?
Yes, even with fees, budget airlines are usually 20-40% cheaper for travelers who pack light and don't need extras. A base fare of $382 might become $432 with a carry-on, still beating full-service airlines at $545.
Should I wait for a sale or book now?
If you see fares around $382 for San Francisco to Chicago, book immediately - that's already 30% below average. Sales rarely go below this unless it's an error fare or last-minute deal.
Ready to book? Compare all available flights on our main San Francisco to Chicago route page for real-time prices and availability.