Best Flights starting from $230
from$230economy
Phoenix (PHX)
Sun, May 31
Roundtrip
Chicago (Any)
Thu, Jun 4
Fields updated — click View Prices to search ↑
Other Destinations
Phoenix (PHX) to Las Vegas (Any) in May from $46
From $46
Phoenix (PHX) to San Diego (SAN) in May from $46
From $46
Phoenix (PHX) to Los Angeles (LAX) in May from $51
From $51
Phoenix (PHX) to Las Vegas (LAS) in May from $52
From $52
Phoenix (PHX) to Cleveland (CLE) in May from $56
From $56
Phoenix (PHX) to Washington, D.C. (BWI) in May from $80
From $80
Flights from Other Cities
Orlando (Any) to Chicago (Any) in May from $46
From $46
Dallas (Any) to Chicago (Any) in May from $48
From $48
Miami (Any) to Chicago (Any) in May from $56
From $56
Los Angeles (Any) to Chicago (Any) in May from $66
From $66
Boston (BOS) to Chicago (Any) in May from $81
From $81
Fort Myers (RSW) to Chicago (Any) in May from $91
From $91
✈️ Flight Guide: Phoenix (PHX) → Chicago (Any)
Complete travel information for your May journey
May is a strategic month to depart Phoenix Sky Harbor International Airport (PHX) en route to Chicago (All Airports) (CHIA). The weather is warming in Phoenix, but it's before the June monsoon; this shoulder season yields a mix of lower airfare and manageable crowds. Travel demand spikes around Memorial Day, so book flights early that depart PHX to secure better fares and convenient schedules.
Departing from Phoenix (PHX) FAQs
A nonstop flight from Phoenix Sky Harbor International Airport (PHX) to Chicago O'Hare or Midway (Chicago (All Airports) (CHIA)) typically takes about 3 hours 35 minutes to 4 hours depending on winds and specific routing. Early May schedules often show multiple morning and evening nonstop options; always check the airline's timetable for exact block time. For real-time durations, compare scheduled flight times on Google Flights or the airline's website before booking.
Yes — several carriers operate nonstop services from Phoenix Sky Harbor International Airport (PHX) to Chicago (All Airports) (CHIA) in May, most commonly to Chicago O'Hare (ORD) and sometimes to Midway (MDW). Airlines such as American, United, and Southwest commonly serve these nonstop routes; frequency increases on weekends. Check for nonstop filters on booking sites to find the best PHX to CHIA nonstop options and to secure the lowest fares.
In May, common ways to reach Phoenix Sky Harbor International Airport (PHX) from downtown include rideshare (Uber/Lyft), airport shuttle, taxi, and the PHX Sky Train from 44th Street/Washington light rail station. Early morning and late evening rideshares can be faster but may incur surge pricing during special events and holiday weekends. Allow at least 45–60 minutes from central Phoenix during peak travel times on Memorial Day weekend in late May.
Baggage fees on PHX to CHIA flights depend on the carrier and fare class; major airlines typically charge for checked bags on basic economy fares, while standard economy may include one bag for certain loyalty members or co-branded credit cardholders. Southwest famously includes two free checked bags; discount carriers like Spirit charge per bag and for carry-on extras. Review the carrier-specific baggage policy before booking and add checked luggage during purchase to save on airport fees.
May is generally a lower-impact month for major runway closures at Phoenix Sky Harbor International Airport (PHX), but seasonal construction and maintenance projects sometimes occur; check the airport notices before travel. Also be aware of increased traffic around Memorial Day and local events, which can affect ground travel times. For the latest advisories, consult the PHX official website and your airline notifications in the week before departure.
As of May travel guidance, most domestic U.S. flights between Phoenix Sky Harbor International Airport (PHX) and Chicago (All Airports) (CHIA) follow standard CDC recommendations but do not require testing or quarantine for vaccinated travelers. Airlines may have their own mask policies or health advisories, so verify with your carrier prior to departure. Keep documentation of vaccination or test results if you plan onward international travel from Chicago.
When arriving to Chicago (All Airports) (CHIA) from Phoenix Sky Harbor International Airport (PHX) in May, expect pleasant spring weather and active city events. If you land at O'Hare (ORD), take the CTA Blue Line for the most reliable downtown transfer; if you arrive at Midway (MDW), the Orange Line and rideshares are convenient options. Consider the proximity to top destinations such as downtown Chicago, Naperville, Evanston, Milwaukee and Indianapolis when planning onward travel.
Arriving at Chicago (Any) FAQs
Choosing between Chicago O'Hare International Airport (ORD) and Midway International Airport (MDW) depends on your final destination in the Chicago metro area. O'Hare (part of Chicago (All Airports) (CHIA)) handles more international and long-haul flights and has extensive ground transit (CTA Blue Line to downtown), while Midway is closer to the South Side and often offers quicker access to downtown via the Orange Line. In May, consider train and traffic conditions for Memorial Day weekend when selecting the best Chicago airport.
May in Chicago typically features mild to warm days and cool evenings, with average highs around the upper 60s to low 70s°F (20–22°C) and a moderate chance of spring rain. Travelers arriving from Phoenix Sky Harbor International Airport (PHX) should pack a light jacket or rain layer for Chicago spring breezes. Check a local forecast before travel for any Memorial Day weekend changes in weather.
Travel time from Chicago O'Hare International Airport (ORD) to downtown Chicago is typically 30–60 minutes by CTA Blue Line or car, depending on traffic. In May, rail service is reliable, but weekend events and rush hour may add time; rideshare or taxi trips can take longer during peak periods. For budget travelers, the CTA Blue Line is the most cost-effective and predictable option.
Late May often includes Memorial Day weekend events, downtown parades and outdoor festivals that can impact road traffic near Chicago (All Airports) (CHIA). Additionally, Major League Baseball home games for the Chicago Cubs (Wrigley Field) and White Sox (Guaranteed Rate Field) are in full swing during May, which can heighten demand for rideshares and rental cars. Plan extra ground time after arrival during busy game days and festival weekends.
After arriving at Midway (Chicago (All Airports) (CHIA)), options to reach nearby suburbs include rental cars, regional Pace buses, Metra trains (from connecting stations), and ride-hailing services. Midway's Orange Line connects to the CTA network; for farther suburbs like Naperville or Evanston, a combination of CTA to Metra or direct rideshare may be fastest in May. Check schedules in advance because weekend service patterns may vary.
1.0.2604.19
May Events & Festivals — Impact on PHX Departures and CHIA Arrivals
May features city-specific events that can influence demand for flights between Phoenix Sky Harbor International Airport (PHX) and Chicago (All Airports) (CHIA). In Phoenix and the surrounding Valley, Cinco de Mayo celebrations and Memorial Day weekend pool/outing events increase local travel. In Chicago, May brings active MLB seasons for the Cubs and White Sox and Memorial Day activities downtown; these events can create spikes in ride-hail demand and rental car reservations. If traveling in May, check local event calendars and reserve transfers early.
Best Time to Fly PHX to CHIA — May Travel Timing & Price Insights
The best time to fly from Phoenix Sky Harbor International Airport (PHX) to Chicago (All Airports) (CHIA) in May is mid-week (Tuesday–Thursday) and early morning departures. Mid-week flights often have lower fares and less congestion at airports; early departures tend to have higher on-time performance due to fewer knock-on delays. Avoid peak travel days around Memorial Day weekend and Friday evening returns if you want lower prices and shorter wait times.
Direct vs Connecting Flights from Phoenix Sky Harbor International Airport (PHX) to Chicago (All Airports) (CHIA) in May
Nonstop flights from Phoenix Sky Harbor International Airport (PHX) to Chicago (All Airports) (CHIA) provide the fastest travel time (about 3h 35m–4h) and are ideal for business travelers and those prioritizing convenience in May. Connecting itineraries often come cheaper and offer more time-of-day flexibility but add layover risk; common connection hubs include Denver (DEN), Dallas-Fort Worth (DFW), and Los Angeles (LAX). For May travel, weigh potential savings against added layover time, especially around Memorial Day weekend when tighter connections can be riskier.
Airline Comparison for PHX to CHIA in May — American, United, Southwest, Spirit & More
Major carriers on the Phoenix Sky Harbor International Airport (PHX) to Chicago (All Airports) (CHIA) corridor include American Airlines, United Airlines, Southwest Airlines, and low-cost options such as Spirit. United and American typically offer multiple daily nonstop options to O'Hare with broad network connections; Southwest often competes on price and includes two free checked bags, which can make a big difference on total trip cost. Spirit generally offers the lowest base fares but charges add-ons for bags and seat selection.
Seasonal Travel Tips for PHX to CHIA in May — Weather, Packing & Airport Advice
May travel between Phoenix Sky Harbor International Airport (PHX) and Chicago (All Airports) (CHIA) requires packing for two climates: sun and heat in Phoenix, and variable spring weather in Chicago. Bring a lightweight jacket, a compact umbrella, and layers to accommodate temperature swings. Book nonrefundable ground services with caution, allow extra time for airport transfers during Memorial Day weekend, and confirm baggage allowances when comparing May fares.
Flight Time & Schedules: Phoenix Sky Harbor International Airport (PHX) to Chicago (All Airports) (CHIA) in May
Nonstop flights from Phoenix Sky Harbor International Airport (PHX) to Chicago (All Airports) (CHIA) typically have block times of about 3 hours 35 minutes to 4 hours. Peak schedule windows in May are early morning departures (6:00–9:00) and evening departures (17:00–21:00), accommodating both business and leisure travelers. Several airlines operate daily nonstop and multiple one-stop options via hubs such as Denver (DEN), Dallas-Fort Worth (DFW), and Los Angeles (LAX).
Cheap Flights PHX to CHIA in May — How to Find and Book
Finding cheap flights from Phoenix Sky Harbor International Airport (PHX) to Chicago (All Airports) (CHIA) in May hinges on timing, flexibility, and carrier selection. Aim to book 3–8 weeks before departure for the best balance of availability and price, and search mid-week departures for lower fares. Use fare alerts, flexible-date calendars, and incognito browsing to compare prices across American, United, Southwest and low-cost carriers like Spirit. Consider one-stop itineraries with quick connections in hub cities to cut costs, but weigh total travel time vs. savings.
Tips
- Set fare alerts on Google Flights and Kayak for PHX to CHIA in May and enable email notifications.
- Be flexible by +/- 3 days to find lower midweek fares; Tuesdays and Wednesdays often yield the cheapest options.
- Compare Southwest (two free checked bags) vs. economy fares on legacy carriers when factoring overall trip cost.
- Consider early-morning flights for lower prices and better on-time performance.