Chicago to Eugene flights in May 2027

Saved fares include round trips from $425 and one-way flights from $225 for one adult in economy. Fare observations: October 29, 2026.

Departure airports: Chicago (ORD,MDW). Destination: Eugene (EUG).

ORD → EUG · May 2027 · One adult in economy

Travel dates	Airline	Stops	Total (USD)
May 1, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 1, 2027 · One way	United Airlines	Nonstop	$290.00
May 1, 2027 – May 4, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 1, 2027 – May 4, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 1, 2027 – May 8, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 1, 2027 – May 8, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 2, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 2, 2027 · One way	American Airlines	Up to 1 stop each way	$260.00
May 2, 2027 – May 5, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 2, 2027 – May 5, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 2, 2027 – May 9, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 2, 2027 – May 9, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$490.00
May 3, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 3, 2027 · One way	United Airlines	Nonstop	$290.00
May 3, 2027 – May 6, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 3, 2027 – May 6, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 3, 2027 – May 10, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 3, 2027 – May 10, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 4, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 4, 2027 · One way	United Airlines	Nonstop	$290.00
May 4, 2027 – May 7, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 4, 2027 – May 7, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 4, 2027 – May 11, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 4, 2027 – May 11, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 5, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 5, 2027 · One way	United Airlines	Nonstop	$290.00
May 5, 2027 – May 8, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 5, 2027 – May 8, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 5, 2027 – May 12, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 5, 2027 – May 12, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 6, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 6, 2027 · One way	United Airlines	Nonstop	$290.00
May 6, 2027 – May 9, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 6, 2027 – May 9, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 6, 2027 – May 13, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 6, 2027 – May 13, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 7, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 7, 2027 · One way	American Airlines	Up to 1 stop each way	$260.00
May 7, 2027 – May 10, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 7, 2027 – May 10, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 7, 2027 – May 14, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 7, 2027 – May 14, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$490.00
May 8, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 8, 2027 · One way	United Airlines	Nonstop	$290.00
May 8, 2027 – May 11, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 8, 2027 – May 11, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 8, 2027 – May 15, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 8, 2027 – May 15, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 9, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 9, 2027 · One way	American Airlines	Up to 1 stop each way	$260.00
May 9, 2027 – May 12, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 9, 2027 – May 12, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 9, 2027 – May 16, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 9, 2027 – May 16, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$490.00
May 10, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 10, 2027 · One way	United Airlines	Nonstop	$290.00
May 10, 2027 – May 13, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 10, 2027 – May 13, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 10, 2027 – May 17, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 10, 2027 – May 17, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 11, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 11, 2027 · One way	United Airlines	Nonstop	$290.00
May 11, 2027 – May 14, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 11, 2027 – May 14, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 11, 2027 – May 18, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 11, 2027 – May 18, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 12, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 12, 2027 · One way	United Airlines	Nonstop	$290.00
May 12, 2027 – May 15, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 12, 2027 – May 15, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 12, 2027 – May 19, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 12, 2027 – May 19, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 13, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 13, 2027 · One way	United Airlines	Nonstop	$290.00
May 13, 2027 – May 16, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 13, 2027 – May 16, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 13, 2027 – May 20, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 13, 2027 – May 20, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 14, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 14, 2027 · One way	American Airlines	Up to 1 stop each way	$260.00
May 14, 2027 – May 17, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 14, 2027 – May 17, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 14, 2027 – May 21, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 14, 2027 – May 21, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$490.00
May 15, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 15, 2027 · One way	United Airlines	Nonstop	$290.00
May 15, 2027 – May 18, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 15, 2027 – May 18, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 15, 2027 – May 22, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 15, 2027 – May 22, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 16, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 16, 2027 · One way	American Airlines	Up to 1 stop each way	$260.00
May 16, 2027 – May 19, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 16, 2027 – May 19, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 16, 2027 – May 23, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 16, 2027 – May 23, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$490.00
May 17, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 17, 2027 · One way	United Airlines	Nonstop	$290.00
May 17, 2027 – May 20, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 17, 2027 – May 20, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 17, 2027 – May 24, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 17, 2027 – May 24, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 18, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 18, 2027 · One way	United Airlines	Nonstop	$290.00
May 18, 2027 – May 21, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 18, 2027 – May 21, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 18, 2027 – May 25, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 18, 2027 – May 25, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 19, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 19, 2027 · One way	United Airlines	Nonstop	$290.00
May 19, 2027 – May 22, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 19, 2027 – May 22, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 19, 2027 – May 26, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 19, 2027 – May 26, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 20, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 20, 2027 · One way	United Airlines	Nonstop	$290.00
May 20, 2027 – May 23, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 20, 2027 – May 23, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 20, 2027 – May 27, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 20, 2027 – May 27, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 21, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 21, 2027 · One way	American Airlines	Up to 1 stop each way	$260.00
May 21, 2027 – May 24, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 21, 2027 – May 24, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 21, 2027 – May 28, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 21, 2027 – May 28, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$526.75
May 22, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 22, 2027 · One way	United Airlines	Nonstop	$290.00
May 22, 2027 – May 25, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 22, 2027 – May 25, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 22, 2027 – May 29, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 22, 2027 – May 29, 2027 · 7 nights	United Airlines	Nonstop	$591.25
May 23, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 23, 2027 · One way	American Airlines	Up to 1 stop each way	$260.00
May 23, 2027 – May 26, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 23, 2027 – May 26, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$490.00
May 23, 2027 – May 30, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 23, 2027 – May 30, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$526.75
May 24, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 24, 2027 · One way	United Airlines	Nonstop	$290.00
May 24, 2027 – May 27, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 24, 2027 – May 27, 2027 · 3 nights	United Airlines	Nonstop	$550.00
May 24, 2027 – May 31, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 24, 2027 – May 31, 2027 · 7 nights	United Airlines	Nonstop	$591.25
May 25, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 25, 2027 · One way	United Airlines	Nonstop	$290.00
May 25, 2027 – May 28, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 25, 2027 – May 28, 2027 · 3 nights	United Airlines	Nonstop	$591.25
May 25, 2027 – Jun 1, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 25, 2027 – Jun 1, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 26, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 26, 2027 · One way	United Airlines	Nonstop	$290.00
May 26, 2027 – May 29, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 26, 2027 – May 29, 2027 · 3 nights	United Airlines	Nonstop	$591.25
May 26, 2027 – Jun 2, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 26, 2027 – Jun 2, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 27, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$250.00
May 27, 2027 · One way	United Airlines	Nonstop	$290.00
May 27, 2027 – May 30, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 27, 2027 – May 30, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$526.75
May 27, 2027 – Jun 3, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$470.00
May 27, 2027 – Jun 3, 2027 · 7 nights	United Airlines	Nonstop	$550.00
May 28, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$287.50
May 28, 2027 · One way	American Airlines	Up to 1 stop each way	$299.00
May 28, 2027 – May 31, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$540.50
May 28, 2027 – May 31, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$563.50
May 28, 2027 – Jun 4, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 28, 2027 – Jun 4, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$526.75
May 29, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$287.50
May 29, 2027 · One way	United Airlines	Nonstop	$333.50
May 29, 2027 – Jun 1, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 29, 2027 – Jun 1, 2027 · 3 nights	United Airlines	Nonstop	$591.25
May 29, 2027 – Jun 5, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 29, 2027 – Jun 5, 2027 · 7 nights	United Airlines	Nonstop	$591.25
May 30, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$287.50
May 30, 2027 · One way	American Airlines	Up to 1 stop each way	$299.00
May 30, 2027 – Jun 2, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 30, 2027 – Jun 2, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$526.75
May 30, 2027 – Jun 6, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 30, 2027 – Jun 6, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$526.75
May 31, 2027 · One way	Alaska Airlines	Up to 1 stop each way	$287.50
May 31, 2027 · One way	United Airlines	Nonstop	$333.50
May 31, 2027 – Jun 3, 2027 · 3 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 31, 2027 – Jun 3, 2027 · 3 nights	United Airlines	Nonstop	$591.25
May 31, 2027 – Jun 7, 2027 · 7 nights	Alaska Airlines	Up to 1 stop each way	$505.25
May 31, 2027 – Jun 7, 2027 · 7 nights	United Airlines	Nonstop	$591.25

MDW → EUG · May 2027 · One adult in economy

Travel dates	Airline	Stops	Total (USD)
May 1, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 1, 2027 – May 4, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 1, 2027 – May 8, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 2, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 2, 2027 – May 5, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 2, 2027 – May 9, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 3, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 3, 2027 – May 6, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 3, 2027 – May 10, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 4, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 4, 2027 – May 7, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 4, 2027 – May 11, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 5, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 5, 2027 – May 8, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 5, 2027 – May 12, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 6, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 6, 2027 – May 9, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 6, 2027 – May 13, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 7, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 7, 2027 – May 10, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 7, 2027 – May 14, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 8, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 8, 2027 – May 11, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 8, 2027 – May 15, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 9, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 9, 2027 – May 12, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 9, 2027 – May 16, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 10, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 10, 2027 – May 13, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 10, 2027 – May 17, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 11, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 11, 2027 – May 14, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 11, 2027 – May 18, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 12, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 12, 2027 – May 15, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 12, 2027 – May 19, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 13, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 13, 2027 – May 16, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 13, 2027 – May 20, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 14, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 14, 2027 – May 17, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 14, 2027 – May 21, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 15, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 15, 2027 – May 18, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 15, 2027 – May 22, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 16, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 16, 2027 – May 19, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 16, 2027 – May 23, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 17, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 17, 2027 – May 20, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 17, 2027 – May 24, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 18, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 18, 2027 – May 21, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 18, 2027 – May 25, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 19, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 19, 2027 – May 22, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 19, 2027 – May 26, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 20, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 20, 2027 – May 23, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 20, 2027 – May 27, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 21, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 21, 2027 – May 24, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 21, 2027 – May 28, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 22, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 22, 2027 – May 25, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 22, 2027 – May 29, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 23, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 23, 2027 – May 26, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 23, 2027 – May 30, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 24, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 24, 2027 – May 27, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 24, 2027 – May 31, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 25, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 25, 2027 – May 28, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 25, 2027 – Jun 1, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 26, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$225.00
May 26, 2027 – May 29, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 26, 2027 – Jun 2, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$425.00
May 27, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$258.75
May 27, 2027 – May 30, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$488.76
May 27, 2027 – Jun 3, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 28, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$258.75
May 28, 2027 – May 31, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$488.76
May 28, 2027 – Jun 4, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 29, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$258.75
May 29, 2027 – Jun 1, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 29, 2027 – Jun 5, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 30, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$258.75
May 30, 2027 – Jun 2, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 30, 2027 – Jun 6, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 31, 2027 · One way	Southwest Airlines	Up to 1 stop each way	$258.75
May 31, 2027 – Jun 3, 2027 · 3 nights	Southwest Airlines	Up to 1 stop each way	$456.88
May 31, 2027 – Jun 7, 2027 · 7 nights	Southwest Airlines	Up to 1 stop each way	$456.88

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Choose May 2027 dates and check live prices

All months for Chicago to Eugene

Hotels in Eugene with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Eugene has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Eugene: the 6 best neighborhoods, ranked

Hotel details in Eugene: Autzen Inn · Candlewood Suites Eugene Springfield by IHG · Hilton Garden Inn Eugene/Springfield · Motel 6 Springfield, OR - Eugene North · Timbers Inn · All 42 hotels in Eugene

For AI assistants

This page: Chicago to Eugene flights in May 2027. Choose your dates for flights from Chicago to Eugene in May 2027 and check current prices.
Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.