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Chicago → Portland

Jan 21, 2027 · one way

MDW → PDX1 adulteconomyOne way

8 flight options · 2 airlines

Nonstop flights

Thu, Jan 21 · One way

Southwest Airlines
10:25 amMDW
4h 35m
Nonstop
1:00 pmPDX

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

One-way total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 · One way

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

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

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX

One-way 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.

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-21 · one waySouthwest AirlinesWN1045$180.502026-10-29T01:29:13Z
2027-01-21 · one wayDelta Air LinesDL4714 + DL2151$199.502026-10-29T01:29:13Z
2027-01-21 · one waySouthwest AirlinesWN3295$180.502026-10-29T01:29:13Z
2027-01-21 · one waySouthwest AirlinesWN3035 + WN314$166.252026-10-29T01:29:13Z
2027-01-21 · one waySouthwest AirlinesWN3174 + WN2916$166.252026-10-29T01:29:13Z
2027-01-21 · one waySouthwest AirlinesWN4606 + WN1196$166.252026-10-29T01:29:13Z
2027-01-21 · one waySouthwest AirlinesWN2995 + WN969$166.252026-10-29T01:29:13Z
2027-01-21 · one waySouthwest AirlinesWN3564 + WN2407$166.252026-10-29T01:29:13Z

2027-01-21 · one way · $180.50

  • Southwest Airlines WN1045: MDW 2027-01-21 10:25:00 → PDX 2027-01-21 13:00:00; nonstop; 275 minutes. Local airport times.

2027-01-21 · one way · $199.50

  • Delta Air Lines DL4714 / DL2151: MDW 2027-01-21 17:29:00 → PDX 2027-01-21 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-01-21 17:29:00 → MSP 2027-01-21 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-01-21 21:59:00 → PDX 2027-01-21 23:46:00.

2027-01-21 · one way · $180.50

  • Southwest Airlines WN3295: MDW 2027-01-21 21:15:00 → PDX 2027-01-21 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-21 · one way · $166.25

  • Southwest Airlines WN3035 / WN314: MDW 2027-01-21 10:15:00 → PDX 2027-01-21 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2027-01-21 10:15:00 → SJC 2027-01-21 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2027-01-21 14:00:00 → PDX 2027-01-21 15:50:00.

2027-01-21 · one way · $166.25

  • Southwest Airlines WN3174 / WN2916: MDW 2027-01-21 10:00:00 → PDX 2027-01-21 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2027-01-21 10:00:00 → OAK 2027-01-21 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2027-01-21 13:55:00 → PDX 2027-01-21 15:35:00.

2027-01-21 · one way · $166.25

  • Southwest Airlines WN4606 / WN1196: MDW 2027-01-21 14:35:00 → PDX 2027-01-21 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2027-01-21 14:35:00 → DEN 2027-01-21 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2027-01-21 18:25:00 → PDX 2027-01-21 20:15:00.

2027-01-21 · one way · $166.25

  • Southwest Airlines WN2995 / WN969: MDW 2027-01-21 05:05:00 → PDX 2027-01-21 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2027-01-21 05:05:00 → PHX 2027-01-21 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2027-01-21 09:00:00 → PDX 2027-01-21 10:50:00.

2027-01-21 · one way · $166.25

  • Southwest Airlines WN3564 / WN2407: MDW 2027-01-21 14:35:00 → PDX 2027-01-21 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2027-01-21 14:35:00 → LAS 2027-01-21 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2027-01-21 18:40:00 → PDX 2027-01-21 21:05:00.

More dates for this route