Cheap Phoenix to Chicago Flights? Insider Deals & Money-Saving Tips
Finding affordable Phoenix flights to Chicago doesn’t require luck—it requires strategy, timing, and insider knowledge. The route between Phoenix Sky Harbor International Airport (PHX) and Chicago’s O’Hare International Airport (ORD) is one of America’s most traveled corridors, which means competition among airlines keeps prices surprisingly competitive when you know where to look. Whether you’re planning a business trip, visiting family, or exploring the Windy City’s architectural wonders, this comprehensive guide reveals the secrets that savvy travelers use to secure the best deals on this popular route.
The Phoenix-to-Chicago flight path represents a golden opportunity for budget-conscious adventurers. With multiple airlines competing for your business and various booking strategies available, you can frequently find round-trip fares for under $200 during shoulder seasons. We’ve compiled insider tactics, timing strategies, and booking hacks that will transform how you approach airfare shopping. From understanding airline pricing algorithms to leveraging hidden city ticketing and price alerts, you’ll discover everything needed to maximize your savings while maintaining flexibility and reliability.
Best Time to Book Your Flight
Timing is everything when hunting for cheap Phoenix flights to Chicago. Research from Kayak and flight data analysts consistently shows that booking 1-3 months in advance yields the lowest average fares on domestic routes. For the PHX-ORD corridor specifically, Tuesday and Wednesday departures typically cost 10-15% less than weekend flights. Airlines release new inventory and adjust pricing early in the week, creating windows of opportunity for alert travelers.
The absolute cheapest booking window falls between 3-6 weeks before departure. This sweet spot allows enough advance planning for airlines to optimize pricing without triggering the premium pricing that occurs during the final two weeks before travel. If you’re flexible with exact dates, you can save substantially by shifting your travel by just one or two days. A Friday departure might cost $280 while the same flight on Thursday costs $190—a difference of nearly $100 that compounds when booking for multiple passengers.
Time of day matters too. Flights departing Phoenix early morning (5-7 AM) or late evening (9 PM-midnight) are consistently cheaper than mid-morning or afternoon departures. While the convenience factor is lower, the savings can exceed 20-30%, making red-eye flights attractive for budget travelers willing to sacrifice some sleep. Chicago’s O’Hare operates around the clock, so arrival times are flexible regardless of when you depart Phoenix.
Comparing Airlines on the PHX-ORD Route
American Airlines, Southwest, United, and Alaska Airlines all compete aggressively on the Phoenix-Chicago route, creating excellent opportunities for fare comparison. Southwest’s famous two free checked bags policy makes it particularly valuable if you’re traveling with luggage, as competing airlines charge $30-35 per bag. However, Southwest typically prices slightly higher upfront, so always calculate total trip cost rather than base fare alone.
United Airlines frequently offers competitive pricing, especially for economy passengers booking light carry-on only. Their hub in Chicago means frequent flights throughout the day, increasing availability and competitive pressure that drives prices down. American Airlines, with its presence in both Phoenix and Chicago, similarly maintains competitive fares to fill aircraft efficiently. Alaska Airlines occasionally offers flash sales and promotional pricing that can undercut competitors by significant margins—following their social media accounts and email list is worthwhile for opportunistic deals.
Budget carriers like Spirit and Frontier occasionally serve this route with rock-bottom fares, sometimes under $100 one-way. However, their fees for carry-ons, seat selection, and boarding add up quickly. Calculate your true all-in cost before committing. A $99 Spirit flight becomes $180+ once you add realistic fees, while a $150 Southwest fare remains $150 with no hidden charges.
Sign up for airline loyalty programs even if you don’t fly frequently. Southwest Rapid Rewards, United MileagePlus, American AAdvantage, and Alaska Mileage Plan members receive email alerts about flash sales and promotional fares. These insider deals often expire within hours, so email notifications give you crucial advantages over casual browsers.
Money-Saving Strategies That Actually Work
Price tracking across multiple dates simultaneously reveals patterns invisible to casual shoppers. Instead of checking one specific date, search a 7-10 day window and identify the cheapest options. You’ll often discover that flying Wednesday instead of Friday saves $50-100, or departing a day earlier unlocks significantly lower fares. This flexibility is your most powerful negotiating tool against airline pricing algorithms.
Clear your browser cookies and search in incognito mode before booking. While airline pricing isn’t directly based on search history (as once rumored), some travel booking sites use cookies to track searches and potentially show higher prices to repeat visitors. Incognito mode ensures you see baseline pricing without manipulation. Additionally, search from different devices or browsers occasionally—prices can vary slightly between platforms.
Mistake fares and flash sales happen regularly on this route. Following Secret Flying and Thrifty Traveler on social media alerts you to unbelievable deals within minutes of discovery. These outlets track pricing anomalies and post them immediately. We’ve seen round-trip Chicago flights from Phoenix for $89-120 during mistake fare events. Act immediately when these appear—they vanish within hours.
Consider booking one-way flights separately if the math works better than round-trip fares. Sometimes Phoenix to Chicago costs $140 one-way while Chicago to Phoenix costs $95 one-way, making two separate bookings cheaper than a $220 round-trip fare. This strategy requires more flexibility but frequently yields savings of $20-50.
Connecting flights through Denver, Dallas, or Las Vegas occasionally offer cheaper fares than direct routes. While you’ll sacrifice convenience and gain 2-4 hours to your journey, savings of $40-80 per person make connections worthwhile for budget-focused travelers. Use Google Flights to toggle “show more options” and reveal all routing possibilities.
Price Tracking Tools and Alerts
Google Flights stands as the gold standard for price monitoring. Set up a price alert for your specific Phoenix-Chicago route, and Google sends email notifications whenever prices drop below your target threshold. Check the “flexible dates” option to see price variations across your travel window. This passive approach means deals come to you rather than requiring constant monitoring.
Hopper analyzes billions of flight prices and predicts whether fares will rise or fall. Their app alerts you when to book specific routes, taking the guesswork out of timing decisions. Hopper’s “price prediction” feature shows whether current prices are historically cheap, moderate, or expensive—invaluable context for decision-making. Premium features provide even more detailed insights, though the free version covers basics effectively.
Set up price alerts on multiple platforms simultaneously. Kayak, Expedia, Skyscanner, and Orbitz each access slightly different inventory and pricing. Comparing alerts across platforms ensures you never miss a deal. Dedicate 10 minutes weekly to reviewing alerts—you’ll develop intuition for fair pricing and recognize exceptional deals instantly.
Airline websites themselves often feature promotional fares before third-party travel sites. Visit Southwest.com, United.com, and AmericanAirlines.com directly to spot sales. Sign up for their email newsletters to receive advance notice of sales and promotions. These direct bookings sometimes include perks unavailable through third-party sites, like airline-specific discounts or bonus loyalty points.
Alternative Airports to Consider
While Phoenix Sky Harbor (PHX) is your primary departure airport, consider Phoenix-Mesa Gateway Airport (AZA) for occasional deals. Located 40 miles southeast of Phoenix, it’s less convenient but sometimes offers significantly cheaper fares. Budget carriers favor this airport, so watch for promotional pricing. The drive time and parking cost must factor into your savings calculation—a $40 cheaper flight loses value if you spend $50 on extra gas and parking.
On the Chicago side, Midway International Airport (MDW) competes with O’Hare (ORD). Southwest favors Midway, so their Chicago fares often route there. Midway sits 10 miles southwest of downtown Chicago, actually closer than O’Hare for many downtown destinations. Checking both airports reveals which routing offers better value for your specific Chicago destination.
When comparing alternative airports, account for ground transportation costs and time. If flying into Midway saves $30 but costs $25 in Uber fare versus $5 from O’Hare, your net savings shrinks to $5. However, if you’re driving or have transportation arranged, airport savings translate directly to your bottom line.
Seasonal Savings Opportunities
Chicago’s winter (November-March) represents peak savings season for Phoenix travelers. Cold weather deters leisure tourists, reducing demand and enabling airlines to discount aggressively. You’ll find the cheapest fares in January and February, with round-trips frequently under $150. Bundle warm clothing and embrace the Windy City’s winter charm while saving substantially.
Spring break season (mid-March through early April) and summer (June-August) bring peak prices as families and students travel. If possible, avoid these periods. Shoulder seasons—April-May and September-October—offer excellent compromise pricing with pleasant weather. You’ll pay more than winter but significantly less than summer while enjoying Chicago’s best climate.
Thanksgiving week and Christmas represent travel nightmares with premium pricing. If visiting for holidays, book 2-3 months in advance and accept that budget fares aren’t available. Flying the day before Thanksgiving or the day after Christmas often saves 30-40% compared to peak holiday dates.
Chicago hosts numerous conferences, conventions, and events that impact hotel availability and occasionally flight prices. When major events occur, hotels fill quickly but flight prices sometimes decrease as business travelers book in advance. Research Chicago’s event calendar and consider timing trips around major events you’re not attending—you’ll avoid crowds while potentially finding cheaper flights.
Labor Day, Memorial Day, and Independence Day weekends spike prices. Flying Tuesday through Thursday of these weeks costs substantially less than Friday-Sunday. Plan accordingly and adjust travel dates slightly when possible.
If you’re exploring other flight options beyond Phoenix-Chicago, check our guides on flights from Houston Texas to Las Vegas Nevada and flights from Atlanta to Las Vegas for comparison strategies applicable across all routes. Similarly, Dallas to Denver flights employ identical booking principles. For broader travel inspiration, explore our resources on best travel destinations in Southeast Asia, top national parks in the USA, and underrated places to travel: discover hidden gems around the world.
FAQ
What’s the cheapest month to fly from Phoenix to Chicago?
January and February typically offer the lowest fares on the Phoenix-Chicago route, with average prices 30-40% below annual averages. Winter weather deters leisure travelers, enabling airlines to discount aggressively. Book during these months for maximum savings.
How far in advance should I book a Phoenix to Chicago flight?
The optimal booking window is 3-6 weeks before departure. This timing allows enough advance planning for airlines to optimize pricing without triggering premium pricing that occurs in the final two weeks. Booking earlier or later typically results in higher fares.
Are budget airlines cheaper on this route?
Budget carriers like Spirit and Frontier offer lower base fares but add significant fees for carry-ons, seat selection, and boarding. Calculate total trip cost including all fees before booking. Traditional carriers like Southwest often provide better value when fees are included.
Should I book a round-trip or one-way flights?
Round-trip fares are usually cheaper, but occasionally booking two one-way flights separately saves money. Always check both options. Google Flights and Kayak make comparing both approaches simple.
What time of day has the cheapest flights?
Early morning (5-7 AM) and late evening (9 PM-midnight) departures are consistently 20-30% cheaper than mid-morning and afternoon flights. Red-eye flights offer maximum savings for travelers willing to sacrifice sleep.
Can I save money flying into Midway instead of O’Hare?
Sometimes. Southwest frequently routes Chicago flights through Midway with competitive pricing. Compare both airports and factor in ground transportation costs. Midway is actually closer to downtown Chicago for many destinations.
How much can I expect to save with these strategies?
Combining multiple strategies—flexible dates, off-season travel, price tracking, and budget airline comparison—typically saves $50-150 per person on Phoenix-Chicago flights. Occasionally, mistake fares and flash sales yield savings exceeding $100 per ticket.