Best Flights starting from $375
from$375economy
Chicago (MDW)
Wed, May 27
Roundtrip
Portland (PDX)
Wed, Jun 3
from$375economy
Chicago (MDW)
Fri, May 29
Roundtrip
Portland (PDX)
Fri, Jun 5
from$385economy
Chicago (MDW)
Thu, May 28
Roundtrip
Portland (PDX)
Thu, Jun 4
from$546economy
Chicago (MDW)
Tue, May 26
Roundtrip
Portland (PDX)
Tue, Jun 2
from$546economy
Chicago (MDW)
Sat, May 30
Roundtrip
Portland (PDX)
Sat, Jun 6
from$546economy
Chicago (MDW)
Sun, May 31
Roundtrip
Portland (PDX)
Sun, Jun 7
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Other Destinations
Chicago (MDW) to Miami (MIA) in May from $80
From $80
Chicago (MDW) to Washington, D.C. (DCA) in May from $104
From $104
Chicago (MDW) to Pensacola (PNS) in May from $136
From $136
Chicago (MDW) to Dallas (DAL) in May from $160
From $160
Chicago (MDW) to New York (Any) in May from $177
From $177
Chicago (MDW) to Detroit (DTW) in May from $191
From $191
Flights from Other Cities
Los Angeles (LAX) to Portland (PDX) in May from $40
From $40
Las Vegas (LAS) to Portland (PDX) in May from $94
From $94
Atlanta (ATL) to Portland (PDX) in May from $105
From $105
San Diego (SAN) to Portland (PDX) in May from $116
From $116
Cleveland (CLE) to Portland (PDX) in May from $119
From $119
Las Vegas (LAS) to Portland (PDX) in May from $128
From $128
✈️ Flight Guide: Chicago (MDW) → Portland (PDX)
Complete travel information for your May journey
May departures from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) benefit from shoulder-season pricing and improving weather. Travelers should monitor CTA Orange Line service for weekend maintenance and reserve airport parking early to secure discounts. For cheap flights, search flexible dates in early- to mid-May and enable price alerts; consider weekday departures for lower fares. Pack layers for Chicago's variable spring weather, check TSA guidelines for carry-on items, and arrive 75–90 minutes before your scheduled domestic flight. Nearby major cities and destinations served from MDW include downtown Chicago, Naperville, Aurora, Rockford, and Milwaukee—use these as alternative pickup/drop-off points or fare search anchors when seeking lower rates. Book now to lock in May MDW to PDX deals and confirm nonstop availability.
Departing from Chicago (MDW) FAQs
In May, Chicago Midway International Airport (MDW) typically offers a limited number of nonstop flights to Portland International Airport (PDX), often increased slightly for late-spring travel demand. Expect principal carriers to schedule 1–3 non-stop round trips per day on peak travel days; check airline schedules and book early for the best nonstop MDW to PDX fares. Use fare alerts and flexible-date searches to capture lower prices and direct flight availability.
The average nonstop flight time from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) is roughly 4 hours and 45 minutes to 5 hours, depending on winds and routing. Flights with one connection often add 1.5–3+ hours of total travel time, so when speed matters choose nonstop options where available. Check real-time schedules for seasonal variations and plan ground transport accordingly.
For May departures, the most efficient ways to reach Chicago Midway International Airport (MDW) are the CTA Orange Line train, rideshare services, airport shuttles, and on-site parking. The Orange Line connects Midway to downtown Chicago in about 25–35 minutes, making it a budget-friendly option; allow extra time for weekend construction or holiday events. If parking, reserve a spot in advance for lower rates and quicker drop-off.
May often sits in the shoulder season between spring break and summer, so Chicago Midway International Airport (MDW) to Portland International Airport (PDX) fares can be more affordable than peak summer months. Early- to mid-May can yield lower prices especially on weekdays; use fare comparison sites, set price alerts, and consider flexible dates for the cheapest MDW to PDX tickets. Booking 3–8 weeks in advance typically balances price and availability for May travel.
Baggage allowances and fees depend on the carrier; most major U.S. airlines charge for the first checked bag on basic economy fares, while main cabin and higher fares include at least one checked bag. For travel in May, review your airline’s policy for weight, size limits, and any seasonal fee changes—carry-on rules are typically unchanged. Prepaying baggage or bundling it with a checked fare can save money, and always confirm rules for sports equipment if you plan outdoor activities in Portland.
In May, expect moderate traffic at Chicago Midway International Airport (MDW) with occasional weather-related delays early or late in the month; spring storms can affect regional schedules. Arrive 90 minutes before domestic flights to clear security with ease, monitor airport alerts for construction or holiday weekend surges, and pack layers as Chicago weather can be variable in May. Sign up for airline text alerts and consider travel insurance for flexible spring travel plans.
May arrivals at Portland International Airport (PDX) offer mild weather and plentiful options for accessing downtown Portland and surrounding destinations. The MAX Red Line provides a cost-effective link to the city center, while rental cars and ride-hailing services support trips to the Columbia River Gorge, Willamette Valley, and Oregon Coast. Expect comfortable spring temperatures and increasing tourist activity; book accommodations and excursions in advance to secure availability and best rates. Nearby major cities commonly accessed from PDX include Vancouver (WA), Salem, Eugene, Bend, and the coastal towns of Astoria and Cannon Beach—use these as bases for exploring Oregon in May.
Arriving at Portland (PDX) FAQs
Portland International Airport (PDX) offers light rail (MAX Red Line), rental cars, rideshares, taxis, and private shuttles as primary ground transportation in May. The MAX Red Line connects PDX to downtown Portland in roughly 40 minutes and runs frequent service; rental facilities and rideshare pick-up areas are well signed. For May travel—when tourism increases—reserve rental cars ahead and consider purchasing TriMet day passes if you'll use public transit in the city and nearby destinations.
May in Portland International Airport (PDX) area is typically mild and increasingly dry, with daytime highs in the mid-60s to low-70s °F (18–22°C) and sporadic spring showers. May is ideal for outdoor activities like Columbia River Gorge hikes and Willamette Valley winery visits, but pack a light rain jacket for early morning or evening drizzle. Monitor local forecasts before travel and plan outdoor excursions with flexible timing due to spring weather variability.
May often represents a shoulder season for Portland lodging, meaning competitive rates near Portland International Airport (PDX) compared with high-summer prices. Business travel and conferences can influence nightly rates, so book in advance and compare hotels near the airport, downtown Portland, and neighborhoods like the Pearl or Alberta for price and convenience. Use package deals and flexible-date searches to find discount rates and consider nearby cities such as Vancouver (WA), Salem, or Bend for alternative lodging options.
From Portland International Airport (PDX), visitors can reach top attractions like the Oregon Museum of Science and Industry (OMSI), Washington Park, the Pearl District, and day trips to the Columbia River Gorge and Mount Hood. May's spring blooms make the Japanese Garden and Lan Su Chinese Garden especially appealing, while food and craft brewery scenes thrive downtown. Plan for a mix of urban exploration and nearby outdoor adventures—book tours and rentals early in May to secure availability.
PDX sees moderate passenger volumes in May as tourism ramps up; arrivals can be smooth by using automated passport control for international travelers and by following signs to baggage claim and ground transport. Domestic arrivals benefit from efficient baggage handling and clear ride-hailing zones; opt for mobile notifications from your airline and enroll in programs like TSA PreCheck for return travel out of Portland. Allow 30–60 minutes from touchdown to ground transport for a stress-free transfer.
In addition to Portland itself, travelers arriving at Portland International Airport (PDX) commonly access Vancouver (WA), Salem, Eugene, Bend, and the Oregon Coast towns like Astoria and Cannon Beach. These destinations serve varied interests from wine country and hiking to coastal getaways; car rentals or regional shuttle services make day trips and multi-city itineraries straightforward. Use PDX as a hub for exploring both urban attractions and Oregon’s natural landscapes in May.
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May Events & Festivals in Portland — What to See After Flying MDW to PDX
May in Portland features spring festivals, outdoor markets, and garden blooms that can increase demand for flights arriving at Portland International Airport (PDX). Look for events like neighborhood open streets, early rose garden blooms at the Portland Japanese Garden, and food/trade festivals that attract regional visitors. These events can raise hotel prices and fill late-weekend flights, so book MDW to PDX travel and accommodations sooner if your trip coincides with a popular festival. Check local event calendars for exact dates and consider midweek travel to avoid peak crowds. CTA: Explore Portland's May event calendar and reserve your MDW to PDX flights and hotels now.
Best Time to Fly MDW to PDX — Optimize Cost and Comfort in May
For May travel from Chicago Midway International Airport (MDW) to Portland International Airport (PDX), the best time to fly is typically midweek (Tuesday–Thursday) and early mornings. These windows often offer lower fares and fewer delays; late-afternoon and weekend flights tend to be pricier due to leisure travel demand. Book within a 3–8 week window for the best May prices, or earlier if you need specific nonstop times. Use flexible-date tools to compare fares across a full month and set alerts for small price drops. CTA: Compare MDW to PDX prices for May weekdays to find the cheapest departures.
Direct vs Connecting Flights — MDW to PDX in May
Choosing nonstop flights from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) in May saves time and reduces connection risk, typically taking about 4 hours 45 minutes to 5 hours. However, connecting flights can be significantly cheaper and offer more schedule flexibility—common connection points include DEN, MSP, and DFW. If price is your main concern, a short one-stop itinerary can lower ticket costs, but build at least a 60–90 minute connection buffer to reduce missed-connection risk. For business travelers or tight itineraries in May, prioritize nonstop options when available; budget travelers may prefer connecting flights to maximize savings. CTA: Evaluate nonstop and one-stop options for May and choose the route that matches your schedule and budget.
Airline Comparison for MDW to PDX — Best Carriers for May Travel
Carriers on the MDW to PDX route include a mix of legacy and low-cost airlines; availability of nonstop service depends on seasonal schedules. Low-cost carriers may offer lower base fares but charge for checked bags and seat selection—factor those fees into your total cost. Legacy carriers often include more frequent flights, loyalty benefits, and better rebooking options in May. For comfort and time-sensitive trips, consider a mainline carrier nonstop; for pure budget travel, select a low-cost airline and prepay for baggage to avoid airport fees. Compare total trip cost (fare + fees), seat comfort, and schedule when choosing an airline for May travel. CTA: Compare carriers for your MDW to PDX May trip and book the option that balances price and convenience.
Seasonal Travel Tips for May — MDW to PDX Route Advice
Pack layered clothing when flying from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) in May—mornings can be cool while afternoons warm up. Bring a light rain shell for spring showers and comfortable walking shoes for exploring Portland neighborhoods and parks. Allow extra time for airport transfers on festival weekends and confirm public transit schedules for holidays and maintenance closures. If you plan outdoor activities like hikes in the Columbia River Gorge or winery tours in the Willamette Valley, reserve guides and rental cars ahead to secure availability. CTA: Prepare for May weather and book MDW to PDX transportation and tours early to ensure the best experience.
Flight Time MDW to PDX — Schedules and Typical Durations in May
Nonstop flights between Chicago Midway International Airport (MDW) and Portland International Airport (PDX) typically take about 4 hours 45 minutes to 5 hours in May. Many itineraries include one connection—common hubs include Denver (DEN), Minneapolis (MSP), and Dallas/Fort Worth (DFW)—which can extend total travel time to 7–10 hours depending on layover length. Prevailing winds and seasonal jet stream shifts in May can slightly alter flight times, so consult live schedules and tracking tools the day of travel. For the best schedules, search for early morning nonstop departures to maximize your arrival day in Portland and avoid late-evening connections. CTA: Check current MDW to PDX schedules and real-time flight status for May.
Cheap Flights MDW to PDX in May — Savings Strategies
To secure cheap flights from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) in May, broaden your search to include flexible travel dates, midweek departures, and nearby airports. Compare non-stop versus one-stop itineraries—sometimes a single short connection can drop the fare substantially. Sign up for price alerts and monitor flash sales from carriers serving MDW and PDX. Consider flying into or out of alternate airports near Chicago or Portland (for example, Chicago O'Hare for added competition or arrival near Eugene for different travel plans) to unlock additional savings. Book 3–8 weeks in advance for the best balance between price and availability, and use fare-trackers to catch May-specific discounts. CTA: Search MDW to PDX cheap flights for May now and set an alert to lock in a low fare.