Cheapest Flights LAX to Chicago: Insider Tips for Budget-Conscious Travelers
Flying from Los Angeles to Chicago doesn’t have to drain your travel budget. This popular cross-country route connects two of America’s most vibrant cities, and with the right strategy, you can find exceptional deals that let you spend more on experiences and less on airfare. Whether you’re heading to the Windy City for business, a weekend getaway, or a longer adventure, understanding how to navigate the LAX to Chicago flight market is essential for savvy travelers.
The distance between Los Angeles International Airport and Chicago’s two major hubs—O’Hare International Airport and Midway International Airport—is approximately 1,745 miles, making it a roughly 3.5 to 4-hour flight. This distance creates a sweet spot for pricing: not so short that driving becomes competitive, but not so long that the route commands premium fares. With major carriers like American, United, Southwest, and Delta competing on this corridor, competition keeps prices relatively reasonable when you know where to look.
In this guide, we’ll reveal the insider secrets that frequent flyers and travel agents use to score the cheapest flights on this route. From timing your search to leveraging airline loyalty programs, these proven tactics will help you maximize your savings and get to Chicago without overspending on transportation.
Best Time to Book LAX to Chicago Flights
The golden window for booking LAX to Chicago flights is typically 1 to 3 months in advance. Research consistently shows that booking too far ahead (more than 3 months) often results in higher prices, as airlines haven’t yet released their most competitive fares. Conversely, booking last-minute rarely yields savings on this competitive route—instead, you’ll typically pay premium prices for the convenience of flexible timing.
For domestic flights on this route, Tuesday and Wednesday tend to offer the lowest fares, as airlines traditionally adjust pricing after weekend travel patterns. Many carriers release their lowest fares on Tuesday mornings, creating a brief window of opportunity for alert travelers. If you can be flexible with your departure day, shifting your travel to a mid-week departure can save you $50 to $150 compared to Friday or Sunday flights.
Time of day also matters significantly. Early morning departures (6 AM to 8 AM) and red-eye flights typically offer lower fares than convenient mid-morning or afternoon departures. While the inconvenience of an early wake-up or overnight flight isn’t for everyone, the savings can be substantial—sometimes 20 to 30 percent cheaper than peak-hour flights. Many business travelers avoid these times, reducing demand and allowing airlines to offer competitive pricing.
Day of the Week Strategy
Understanding which days travelers avoid is crucial for finding cheap flights LAX to Chicago. Mondays and Saturdays are typically more expensive because they accommodate both weekend leisure travelers and those extending their trips. Tuesday through Thursday are consistently cheaper, with Wednesday often being the absolute cheapest day to fly this route.
The psychology of business travel influences these patterns significantly. Most business travelers prefer Monday morning departures to start their work week and Friday afternoon returns to extend their weekends. By positioning your travel around these patterns—perhaps flying Tuesday evening instead of Monday morning—you’ll access the lower fares that leisure travelers often miss.
For return flights, the same principle applies. A Wednesday or Thursday return will cost substantially less than a Sunday return, when everyone heads home after their weekend. If your Chicago trip allows flexibility, consider staying through a Wednesday and flying home Thursday; the savings on your return flight often exceed any additional hotel night costs.
Airline Comparison and Direct vs. Connecting Flights
Southwest Airlines has historically offered competitive pricing on the LAX-Chicago route, partly due to their free checked bag policy and no change fees. This transparency means you’re getting better overall value even if the base fare isn’t always the absolute lowest. United Airlines operates multiple daily flights from LAX to both O’Hare and Midway, creating competitive pressure that benefits fare-conscious travelers.
American Airlines and Delta also compete aggressively on this route, particularly if you’re flying from LAX to O’Hare, which is American’s hub. The competition among these four major carriers keeps prices reasonable throughout the year. However, you should always compare the total cost, not just the base fare. Some airlines charge for checked bags, seat selection, and even carry-on luggage, which can significantly increase your actual cost.
Direct flights command a premium compared to one-stop itineraries, typically costing $30 to $80 more per leg. If you have time flexibility, a connecting flight through Denver, Dallas, or Kansas City can yield substantial savings. The trade-off is roughly 1 to 2 additional hours of travel time, but budget-conscious travelers often find this worthwhile. Connecting flights through major hubs can open up more competitive pricing options across multiple carriers.
Alternative Airports and Hidden Strategies
While LAX is your departure point, you have more flexibility on your arrival. Chicago has two major commercial airports: O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW). Midway is often 15 to 40 percent cheaper than O’Hare, and it’s only about 30 minutes from downtown Chicago by public transit or rideshare. Checking fares to both airports before booking can reveal significant savings.
Some travelers also consider flying into Gary International Airport (GYG), Indiana, about 30 miles southeast of Chicago. While it offers fewer flight options, when flights are available, they’re occasionally cheaper than both major Chicago airports. The additional ground transportation cost usually makes this worthwhile only if the flight savings exceed $100.
Another advanced strategy involves using price comparison tools and understanding why flight prices fluctuate. Sometimes flying into a nearby city and renting a car for a short drive costs less than a direct flight to your final destination. This is particularly true during peak travel periods when Chicago airport prices spike dramatically.
Price Tracking Tools and Alerts
Modern travel technology makes finding cheap flights LAX to Chicago easier than ever. Google Flights, Kayak, and Skyscanner all offer price tracking features that alert you when fares drop on your desired route. Set up alerts for your preferred travel dates, and you’ll receive notifications when prices change—allowing you to book when fares dip.
Hopper uses historical data and machine learning to predict whether prices will rise or fall, telling you the optimal booking window for your specific dates. Airfarewatchdog is another excellent resource that specializes in finding exceptional deals and notifying subscribers of sales. These tools are free to use and can save you hundreds of dollars by catching temporary price reductions.
Browser extensions like Honey and Capital One Shopping automatically check for better prices while you’re booking, ensuring you’re not missing available discounts. Many travelers make the mistake of booking immediately after finding a decent fare, when waiting just 24 to 48 hours might reveal even better pricing. Setting up automated alerts removes the need for manual checking and ensures you never miss a sale.
Seasonal Patterns and Peak Travel Times
LAX to Chicago fares follow predictable seasonal patterns. Summer (June through August) is peak travel season, with fares 20 to 50 percent higher than winter months. If possible, avoid traveling during summer school breaks, major holidays, and spring break. These periods see the highest demand and the highest corresponding prices.
The cheapest time to fly this route is typically January through early March and September through November. These shoulder seasons offer pleasant weather in both cities while avoiding the extreme demand that drives up prices. A flight booking in January might cost $150 to $200 less than the identical flight in July, representing a 30 to 40 percent savings.
Thanksgiving week and the two weeks surrounding Christmas are extremely expensive, with prices sometimes doubling compared to normal periods. If you must travel during holidays, book at least 6 to 8 weeks in advance and consider flying on the actual holiday (Thanksgiving Day or Christmas Day), when fewer people travel. These unusual travel days often feature significantly lower fares.
Maximizing Loyalty Programs and Credit Cards
If you fly regularly, joining airline loyalty programs is essential. United MileagePlus, American AAdvantage, and Southwest Rapid Rewards all offer ways to earn free flights on the LAX-Chicago route. Accumulating miles through credit card sign-up bonuses can provide your next flight free or heavily discounted. A premium travel credit card can pay for itself through airline credits and lounge access alone.
Many travelers overlook the power of airline credit cards for this specific route. The sign-up bonus on cards like the United Gateway or Southwest Rapid Rewards card often provides 50,000 to 75,000 miles, which equals one or more free flights to Chicago. Even if you don’t fly frequently, these bonuses can provide substantial value on this single trip.
Co-branded credit cards also offer valuable perks like free checked bags, priority boarding, and seat selection upgrades. These benefits increase your overall value even if the base fare isn’t the absolute lowest. When combined with other strategies mentioned in this guide, loyalty program benefits can reduce your effective cost to nearly nothing on future trips.
Additionally, consider exploring how other competitive routes handle pricing to understand broader airline strategies. The tactics that work for LAX-Chicago often apply to other popular domestic routes as well.
Once you’ve booked your cheap flight to Chicago, enhance your trip by exploring the city’s incredible attractions. The Art Institute of Chicago, Navy Pier, and the iconic Cloud Gate sculpture offer world-class experiences. For broader travel inspiration, exploring top national parks in the USA can inspire extended road trips from Chicago.
FAQ
What’s the average price for flights from LAX to Chicago?
Average round-trip fares range from $250 to $400 depending on season and how far in advance you book. Off-season prices can drop to $150 to $250, while peak summer fares often reach $400 to $600 or higher. Booking 1 to 3 months in advance typically yields the best prices.
Which airlines offer the cheapest flights on this route?
Southwest, United, American, and Delta all compete aggressively on LAX-Chicago flights. Prices vary by date and season, so comparing all four is essential. Southwest’s transparent pricing (no hidden fees) often provides the best overall value, while budget carriers occasionally offer deals but typically charge extra fees that eliminate savings.
Is it cheaper to fly into Midway or O’Hare?
Chicago Midway (MDW) is typically 15 to 40 percent cheaper than O’Hare (ORD), and it’s only 30 minutes from downtown by public transit. Always check both airports before booking, as the savings can be substantial and ground transportation costs are minimal.
Should I book a round-trip or two separate one-way tickets?
For most LAX-Chicago flights, round-trip bookings are cheaper than purchasing two one-way tickets separately. The exception occurs when one-way fares drop dramatically due to airline sales. Use price comparison tools to check both options before committing.
What’s the best day of the week to fly LAX to Chicago?
Tuesday through Thursday offer the cheapest fares, with Wednesday typically being the absolute cheapest. Early morning and red-eye flights also cost significantly less than convenient mid-morning or afternoon departures.
How far in advance should I book?
The sweet spot is 1 to 3 months in advance. Booking too early (more than 3 months) often results in higher prices, while last-minute bookings rarely offer savings on this competitive route. Set price alerts and book when fares drop within your preferred travel window.
Can I use airline miles for LAX-Chicago flights?
Yes, all major airlines allow award bookings on this route, typically requiring 25,000 to 50,000 miles for a one-way domestic flight depending on the carrier and season. Credit card sign-up bonuses often provide enough miles for a free round-trip flight on this route.
