Travel with Axel,
get the best price.

Route overview: Chicago to Portland (PDX) flight deals

Chicago → Portland

Jan 20, 2027 · return Feb 3, 2027

MDW → PDX1 adulteconomyRound trip

6 flight options · 2 airlines

One-stop flights

Wed, Jan 20 – Wed, Feb 3

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jan 20 – Wed, Feb 3

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Jan 20 – Wed, Feb 3

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jan 20 – Wed, Feb 3

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jan 20 – Wed, Feb 3

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jan 20 – Wed, Feb 3

Southwest Airlines
10:10 amMDW
4h 35m
Nonstop
12:45 pmPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ PDX

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

Explore this route

All dates for this routeJan 19, 2027 → Feb 2, 2027Jan 21, 2027 → Feb 4, 2027
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Route overview: Chicago to Portland (PDX) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-20 → 2027-02-03Southwest AirlinesWN4606 + WN1196 / WN510 + WN576$313.502026-10-29T01:29:13Z
2027-01-20 → 2027-02-03Delta Air LinesDL4714 + DL2151 / DL411 + DL4684$370.502026-10-29T01:29:13Z
2027-01-20 → 2027-02-03Southwest AirlinesWN3035 + WN314 / WN510 + WN576$313.502026-10-29T01:29:13Z
2027-01-20 → 2027-02-03Southwest AirlinesWN3174 + WN2916 / WN510 + WN576$313.502026-10-29T01:29:13Z
2027-01-20 → 2027-02-03Southwest AirlinesWN2995 + WN969 / WN510 + WN576$313.502026-10-29T01:29:13Z
2027-01-20 → 2027-02-03Southwest AirlinesWN2087 / WN510 + WN576$327.752026-10-29T01:29:13Z

2027-01-20 → 2027-02-03 · $313.50

  • Southwest Airlines WN4606 / WN1196: MDW 2027-01-20 14:35:00 → PDX 2027-01-20 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2027-01-20 14:35:00 → DEN 2027-01-20 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2027-01-20 18:25:00 → PDX 2027-01-20 20:15:00.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

2027-01-20 → 2027-02-03 · $370.50

  • Delta Air Lines DL4714 / DL2151: MDW 2027-01-20 17:29:00 → PDX 2027-01-20 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-01-20 17:29:00 → MSP 2027-01-20 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-01-20 21:59:00 → PDX 2027-01-20 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2027-02-03 23:20:00 → MDW 2027-02-04 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-02-03 23:20:00 → DTW 2027-02-04 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-02-04 09:10:00 → MDW 2027-02-04 09:46:00.

2027-01-20 → 2027-02-03 · $313.50

  • Southwest Airlines WN3035 / WN314: MDW 2027-01-20 10:15:00 → PDX 2027-01-20 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2027-01-20 10:15:00 → SJC 2027-01-20 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2027-01-20 14:00:00 → PDX 2027-01-20 15:50:00.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

2027-01-20 → 2027-02-03 · $313.50

  • Southwest Airlines WN3174 / WN2916: MDW 2027-01-20 10:00:00 → PDX 2027-01-20 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2027-01-20 10:00:00 → OAK 2027-01-20 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2027-01-20 13:55:00 → PDX 2027-01-20 15:35:00.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

2027-01-20 → 2027-02-03 · $313.50

  • Southwest Airlines WN2995 / WN969: MDW 2027-01-20 05:05:00 → PDX 2027-01-20 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2027-01-20 05:05:00 → PHX 2027-01-20 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2027-01-20 09:00:00 → PDX 2027-01-20 10:50:00.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

2027-01-20 → 2027-02-03 · $327.75

  • Southwest Airlines WN2087: MDW 2027-01-20 10:10:00 → PDX 2027-01-20 12:45:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

Explore this route