Category: <span>Chicago</span>

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.

Click for more details and booking links Nonstop Flights: Portland to/from Chicago $179-$197 r/t [May-February] – American Airlines

Airfare Deals American Airlines Chicago Flights from Chicago / Milwaukee Flights from Portland Oneworld

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.

Click for more details and booking links Nonstop Flights: Portland to/from (Chicago $179) or (Denver $139) r/t [April-June] (Tue, Wed, Sat) – United / Alaska Airlines / American Airlines

Airfare Deals Alaska Airlines American Airlines Chicago Flights from Portland Oneworld Star Alliance United

Airfare Deals Alaska Airlines Chicago Flights from Chicago / Milwaukee Flights from Seattle

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.

Click for more details and booking links Nonstop Flights: Seattle to/from Chicago $107-$123 r/t [March-April] – United / Alaska Airlines

Airfare Deals Alaska Airlines Chicago Flights from Chicago / Milwaukee Flights from Seattle Star Alliance United

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.

Click for more details and booking links Nonstop Flights: Denver to/from Chicago, Phoenix, or Charlotte, North Carolina $119-$157 r/t [April-May] (Tue, Wed, Sat) – American Airlines / United

Airfare Deals American Airlines Chicago Flights from Denver Oneworld Star Alliance United

Airfare Deals Chicago Flights from Chicago / Milwaukee Flights from Denver Star Alliance United

Airfare Deals Chicago Delta Flights from Seattle SkyTeam Star Alliance United

Airfare Deals American Airlines Chicago Flights from Chicago / Milwaukee Flights from Portland Oneworld

Airfare Deals American Airlines Chicago Flights from Chicago / Milwaukee Flights from Seattle Oneworld

Airfare Deals Alaska Airlines Chicago Delta Flights from Chicago / Milwaukee Flights from Seattle SkyTeam Star Alliance United

Airfare Deals American Airlines Chicago Flights from Phoenix Oneworld

Airfare Deals Chicago Delta Flights from Chicago / Milwaukee Flights from New York SkyTeam Star Alliance United

Airfare Deals Chicago Delta Flights from Chicago / Milwaukee Flights from Seattle SkyTeam

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.

Click for more details and booking links Nonstop Flights: Seattle to/from Chicago $105-$152 r/t [February-April] (Cheapest flights depart/return Saturday) – United / Delta

Airfare Deals Chicago Delta Flights from Chicago / Milwaukee Flights from Seattle SkyTeam Star Alliance United

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.

Click for more details and booking links Nonstop Flights: Phoenix to/from Chicago $138-$178 r/t [January-March] – United / American Airlines

Airfare Deals American Airlines Chicago Flights from Chicago / Milwaukee Flights from Phoenix Oneworld Star Alliance United

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.

Click for more details and booking links Nonstop Flights: Seattle to/from Chicago $138 r/t [January-March] – Delta

Airfare Deals Chicago Delta Flights from Seattle SkyTeam

Airfare Deals Alaska Airlines Chicago Flights from Chicago / Milwaukee Flights from Seattle Star Alliance United

Airfare Deals Alaska Airlines Chicago Delta Flights from Chicago / Milwaukee Flights from Seattle SkyTeam

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).

Click for more details and booking links Nonstop Flights: New York to/from Chicago $124 r/t [August-November] – American Airlines / United

Airfare Deals American Airlines Chicago Flights from Chicago / Milwaukee Flights from New York Oneworld Star Alliance United

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.

Click for more details and booking links Nonstop Flights: Seattle to/from Chicago $158 r/t [March-May] – United / Delta / Alaska Airlines

Airfare Deals Alaska Airlines Chicago Flights from Chicago / Milwaukee Flights from Seattle Star Alliance United