American Airlines has round-trip flights from Portland (PDX) to Chicago (ORD) for $179-$197, NONSTOP. Flights May to February. No Monday departures. Extended weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
United, Alaska Airlines, and American Airlines have round-trip flights from Portland (PDX) to Chicago or Denver (ORD, DEN) for $139-$179, NONSTOP. Flights April to June. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American and Alaska Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Alaska Airlines has round-trip flights from Seattle (SEA) to Chicago (ORD) for $117, NONSTOP. Flights April to May. Very few weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on Alaska Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
United and Alaska Airlines have round-trip flights from Seattle (SEA) to Chicago (ORD) for $107-$123, NONSTOP. Flights March to April. Extended weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on Alaska Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
American Airlines and United have round-trip flights from Denver (DEN) to Chicago, Phoenix, or Charlotte, North Carolina (ORD, PHX, CLT) for $119-$157, NONSTOP. Flights April to May. Extended weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
United has round-trip flights from Denver (DEN) to Chicago (ORD) for $117-$126, NONSTOP. Flights in March. No Sunday departures. Weekends available. Origin/Destination reversible.
United’s “Basic Economy” fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.
United and Delta have round-trip flights from Seattle (SEA) to Chicago (ORD) for $148-$153, NONSTOP. Flights October to March. No Monday departures. Extended weekends available. Origin/Destination reversible.
American Airlines and United have round-trip flights from Portland (PDX) to Chicago (ORD) for $150, NONSTOP. Flights January to February. Extended weekends available. Origin/Destination reversible.
American Airlines has round-trip flights from Seattle (SEA) to Chicago (ORD) for $126, NONSTOP. Flights September to February. Weekends available. Origin/Destination reversible.
Alaska Airlines, United, and Delta have round-trip flights from Seattle (SEA) to Chicago (ORD) for $168, NONSTOP. Flights September to December. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. No Christmas dates available.
American Airlines has round-trip flights from Phoenix (PHX) to Chicago (ORD) for $168-$173, NONSTOP. Flights August to November. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates. Most flights are on Tuesdays, Wednesdays, or Saturdays.
United and Delta have round-trip flights from New York (LGA) to Chicago (ORD) for $106, NONSTOP. Flights August to December. Very few extended weekends available. Origin/Destination reversible. No Christmas dates available.
Delta has round-trip flights from Seattle (SEA) to Chicago (ORD) for $148-$183, NONSTOP. Flights September to December. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. No Christmas dates available.
United and Delta have round-trip flights from Seattle (SEA) to Chicago (ORD) for $105-$152, NONSTOP. Flights February to April. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. The cheapest flights are on Saturdays only.
A Carry-on bag and also a personal item is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
United and American Airlines have round-trip flights from Phoenix (PHX) to Chicago (ORD) for $138-$178, NONSTOP. Flights January to March. Weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Midweek flights are the less expensive at $138, weekend flights are more expensive at $178.
Delta has round-trip flights from Seattle (SEA) to Chicago (ORD) for $138, NONSTOP. Flights January to March. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible.
We are maintaining a consolidated list of every Cyber Monday fare that is below its 6-month moving price average and also below $198 (linked). Use it if you want a quick overview of every fare that we consider to be at a worthwhile discount.
United and Alaska Airlines have round-trip flights from Seattle (SEA) to Chicago (ORD) for $178, NONSTOP. Flights November to March. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. Holiday blackouts.
Alaska Airlines and Delta have round-trip flights from Seattle (SEA) to Chicago (ORD) for $178-$198, NONSTOP. Flights September to December. Extended weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
American Airlines and United have round-trip flights from New York (LGA) to Chicago (ORD) for $124, NONSTOP. Flights August to November. Extended weekends available.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
United’s “Basic Economy” fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding. If you have the United Explorer credit-card, use the “free checked bag” perk.
The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).
United, Delta, and Alaska Airlines have round-trip flights from Seattle (SEA) to Chicago (ORD) for $158, NONSTOP. Flights March to May. Very few weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on Delta and Alaska Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
