Category: <span>Chicago</span>

Nonstop Flights: Seattle to Chicago, San Francisco, San Jose, or Los Angeles $92-$128 r/t [January-March] – Southwest / Delta / American / Alaska Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published November 29, 2024 by

Nonstop Flights: Seattle to Chicago, San Francisco, San Jose, or Los Angeles $92-$128 r/t [January-March] – Southwest / Delta / American / Alaska Airlines

Southwest, Delta, American, and Alaska Airlines have round-trip flights from Seattle (SEA) to Chicago (MDW/ORD, SFO, SJC, LAX) for $92-$128, NONSTOP. Flights January to March. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available.

Some small OTAs on Skyscanner have this for cheaper than the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.

For Alaska Airlines fares, you will need to use the coupon-code BFSALE30 for their fares to be competitive to the other airlines.

Click for more details and booking links Nonstop Flights: Seattle to Chicago, San Francisco, San Jose, or Los Angeles $92-$128 r/t [January-March] – Southwest / Delta / American / Alaska Airlines

Airfare Deals Chicago Flights from Seattle Southwest

Nonstop Flights: Seattle to/from Chicago, Fort Lauderdale, Miami, Tampa, or St. Louis $143-$177 r/t [October-January] (Weekends available) – United / Delta / Southwest
Image Credits: Daniel Schwen, Creative Commons 4.0
Published October 1, 2024 by

Nonstop Flights: Seattle to/from Chicago, Fort Lauderdale, Miami, Tampa, or St. Louis $143-$177 r/t [October-January] (Weekends available) – United / Delta / Southwest

United, Delta, and Southwest, have round-trip flights from Seattle (SEA) to Chicago, Fort Lauderdale, Miami, Tampa, or St. Louis (ORD, MIA, TPA, STL) for $143-$149, NONSTOP. Flights October to January. 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.

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: Seattle to/from Chicago, Fort Lauderdale, Miami, Tampa, or St. Louis $143-$177 r/t [October-January] (Weekends available) – United / Delta / Southwest

Airfare Deals Chicago Flights from Seattle Star Alliance United

Nonstop Flights: Los Angeles to/from Chicago, Denver, Houston, Phoenix, or Dallas $134 r/t [October-January] – Southwest
Image Credits: Daniel Schwen, Creative Commons 4.0
Published October 1, 2024 by

Nonstop Flights: Los Angeles to/from Chicago, Denver, Houston, Phoenix, or Dallas $134 r/t [October-January] – Southwest

Southwest has round-trip flights from Los Angeles (LAX) to Chicago, Denver,  Houston, or Dallas (MDW, DEN, HOU, DAL) for $134, NONSTOP. Flights October to January. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible.

Other domestic destinations are also priced about 10%-15% lower than their moving averages, good, but not great.

Click for more details and booking links Nonstop Flights: Los Angeles to/from Chicago, Denver, Houston, Phoenix, or Dallas $134 r/t [October-January] – Southwest

Airfare Deals Chicago Flights from Los Angeles Southwest

Nonstop Flights: New York to/from Chicago or Houston $77-$108 r/t [September-November] (Cheapest fares on Tue/Wed) – JetBlue
Image Credits: Katie Haugland Bowen
Published September 16, 2024 by

Nonstop Flights: New York to/from Chicago or Houston $77-$108 r/t [September-November] (Cheapest fares on Tue/Wed) – JetBlue

JetBlue has round-trip flights from New York (JFK) to Chicago or Houston (ORD, IAH) for $77-$108, NONSTOP. Flights September to November. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.

Cheapest fares are Midweek departures.

JetBlue’s “Basic” fares only allow a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. A regular sized carry-on bag will incur a bag fee. To avoid bag fees, consider using a credit card with the “first free checked bag” perk.

Click for more details and booking links Nonstop Flights: New York to/from Chicago or Houston $77-$108 r/t [September-November] (Cheapest fares on Tue/Wed) – JetBlue

Airfare Deals Chicago Flights from New York JetBlue

Nonstop Flights: Portland to/from Chicago $137-$166 r/t [September-December] (No Christmas) – United
Image Credits: Daniel Schwen, Creative Commons 4.0
Published August 23, 2024 by

Nonstop Flights: Portland to/from Chicago $137-$166 r/t [September-December] (No Christmas) – United

United has round-trip flights from Portland (PDX) to Chicago (ORD) for $137-$166, NONSTOP. Flights September to December. Extended weekends available. Origin/Destination reversible. No Christmas dates available.

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.

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: Portland to/from Chicago $137-$166 r/t [September-December] (No Christmas) – United

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

Nonstop Flights: Seattle to/from Chicago $124-$137 r/t [September-December] (No Christmas) – Alaska Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published August 23, 2024 by

Nonstop Flights: Seattle to/from Chicago $124-$137 r/t [September-December] (No Christmas) – Alaska Airlines

Alaska Airlines has round-trip flights from Seattle (SEA) to Chicago (ORD) for $137, NONSTOP. Flights September to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available. Origin/Destination reversible. No Christmas dates available.

Some small OTAs on Skyscanner and Google have this for as low as $124; which is cheaper than the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.

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 $124-$137 r/t [September-December] (No Christmas) – Alaska Airlines

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

Nonstop Flights: Atlanta to/from Chicago or Denver $107-$114 r/t [August-December] (No Christmas) – United
Image Credits: Larry Johnson, Creative Commons 2.0
Published July 30, 2024 by

Nonstop Flights: Atlanta to/from Chicago or Denver $107-$114 r/t [August-December] (No Christmas) – United

United has round-trip flights from Atlanta (ATL) to Chicago or Denver (ORD, DEN) for $107-$114, NONSTOP. Flights August to December. Extended weekends available. Origin/Destination reversible. No Christmas dates available.

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.

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: Atlanta to/from Chicago or Denver $107-$114 r/t [August-December] (No Christmas) – United

Airfare Deals Chicago Flights from Atlanta Star Alliance United

Nonstop Flights: New York to/from Chicago $92-$106 r/t [August-November] (No Thanksgiving) – Southwest
Image Credits: Daniel Schwen, Creative Commons 4.0
Published July 30, 2024 by

Nonstop Flights: New York to/from Chicago $92-$106 r/t [August-November] (No Thanksgiving) – Southwest

Airfare Deals Chicago Flights from Chicago / Milwaukee Flights from New York Southwest

Nonstop Flights: Seattle to/from Chicago $120-$141 r/t [September-October] (No Thanksgiving) – Southwest
Image Credits: Daniel Schwen, Creative Commons 4.0
Published July 30, 2024 by

Nonstop Flights: Seattle to/from Chicago $120-$141 r/t [September-October] (No Thanksgiving) – Southwest

Airfare Deals Chicago Flights from Chicago / Milwaukee Flights from Seattle Southwest

Nonstop Flights: Denver to/from Chicago $139 r/t [August-December] (No Christmas) – United / American Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published July 29, 2024 by

Nonstop Flights: Denver to/from Chicago $139 r/t [August-December] (No Christmas) – United / American Airlines

United and American Airlines have round-trip flights from Denver (DEN) to Chicago (ORD) for $139, NONSTOP. Flights August to December. Very few weekends available. Origin/Destination reversible. No Christmas dates 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.

Click for more details and booking links Nonstop Flights: Denver to/from Chicago $139 r/t [August-December] (No Christmas) – United / American Airlines

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

Nonstop Flights: Portland to/from Chicago $179-$197 r/t [August-November] (Thanksgiving dates) – Alaska Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published July 23, 2024 by

Nonstop Flights: Portland to/from Chicago $179-$197 r/t [August-November] (Thanksgiving dates) – Alaska Airlines

Alaska Airlines has round-trip flights from Portland (PDX) to Chicago (ORD) for $179-$197, NONSTOP. Flights August to November. Weekends available. Origin/Destination reversible. Dates over Thanksgiving are available.

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: Portland to/from Chicago $179-$197 r/t [August-November] (Thanksgiving dates) – Alaska Airlines

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

Nonstop Flights: New York/Newark to/from Chicago $109-$118 r/t [July] – Delta / JetBlue / United
Image Credits: Daniel Schwen, Creative Commons 4.0
Published June 19, 2024 by

Nonstop Flights: New York/Newark to/from Chicago $109-$118 r/t [July] – Delta / JetBlue / United

Delta, JetBlue, and United have round-trip flights from New York/Newark (LGA/JFK/EWR) to Chicago (ORD) for $109-$118, NONSTOP. Flights in July. No Saturday departures. Very few weekends available. Origin/Destination reversible.

A Carry-on bag and also a personal item is allowed for free on Delta. 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: New York/Newark to/from Chicago $109-$118 r/t [July] – Delta / JetBlue / United

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

Nonstop Flights: Portland to/from Chicago $177-$189 r/t [August-November] (No Thanksgiving) – American Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published June 5, 2024 by

Nonstop Flights: Portland to/from Chicago $177-$189 r/t [August-November] (No Thanksgiving) – American Airlines

American Airlines has round-trip flights from Portland (PDX) to Chicago (ORD) for $177-$189, NONSTOP. Flights August to November. Very few weekends available. Origin/Destination reversible. No Thanksgiving dates.

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 $177-$189 r/t [August-November] (No Thanksgiving) – American Airlines

Airfare Deals American Airlines Chicago Flights from Portland Oneworld

Nonstop Flights: New York/Newark to/from Chicago or Orlando $117-$133 r/t [June-November] (No Thanksgiving) – Delta / American Airlines / Southwest / United
Image Credits: Daniel Schwen, Creative Commons 4.0
Published June 4, 2024 by

Nonstop Flights: New York/Newark to/from Chicago or Orlando $117-$133 r/t [June-November] (No Thanksgiving) – Delta / American Airlines / Southwest / United

Delta, United, American Airlines, and Southwest have round-trip flights from New York/Newark (LGA/EWR/JFK) to Chicago or Orlando (ORD/MDW, MCO) for $119-$133, NONSTOP. Flights June to November. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.

A Carry-on bag and also a personal item is allowed for free on Delta. 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: New York/Newark to/from Chicago or Orlando $117-$133 r/t [June-November] (No Thanksgiving) – Delta / American Airlines / Southwest / United

Airfare Deals American Airlines Chicago Delta Flights from New York Oneworld SkyTeam Southwest

Nonstop Flights: Atlanta to/from Chicago $117-$120 r/t [July-November] (No Thanksgiving) – Delta / United
Image Credits: Daniel Schwen, Creative Commons 4.0
Published May 29, 2024 by

Nonstop Flights: Atlanta to/from Chicago $117-$120 r/t [July-November] (No Thanksgiving) – Delta / United

Delta and United have round-trip flights from Atlanta (ATL) to Chicago (MDW/ORD) for $117-$120, NONSTOP. Flights July to November. Very few weekends available. Origin/Destination reversible. No Thanksgiving dates.

A Carry-on bag and also a personal item is allowed for free on Delta. 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: Atlanta to/from Chicago $117-$120 r/t [July-November] (No Thanksgiving) – Delta / United

Airfare Deals Chicago Delta Flights from Atlanta SkyTeam Star Alliance United

Nonstop Flights: Los Angeles to/from Chicago $151 r/t [August-November] (No Thanksgiving) – United
Image Credits: Daniel Schwen, Creative Commons 4.0
Published May 29, 2024 by

Nonstop Flights: Los Angeles to/from Chicago $151 r/t [August-November] (No Thanksgiving) – United

United has round-trip flights from Los Angeles (LAX) to Chicago (ORD) for $151, NONSTOP. Flights August to November. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.

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.

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: Los Angeles to/from Chicago $151 r/t [August-November] (No Thanksgiving) – United

Airfare Deals Chicago Flights from Los Angeles Star Alliance United

Nonstop Flights: Portland to/from Chicago $179-$197 r/t [May-February] – American Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published April 19, 2024 by

Nonstop Flights: Portland to/from Chicago $179-$197 r/t [May-February] – American Airlines

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

Nonstop Flights: Portland to/from (Chicago $179) or (Denver $139) r/t [April-June] (Tue, Wed, Sat) – United / Alaska Airlines / American Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published March 19, 2024 by

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

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

Nonstop Flights: Seattle to/from Chicago $117 r/t [April-May] – Alaska Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published March 15, 2024 by

Nonstop Flights: Seattle to/from Chicago $117 r/t [April-May] – Alaska Airlines

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

Nonstop Flights: Seattle to/from Chicago $107-$123 r/t [March-April] – United / Alaska Airlines
Image Credits: Daniel Schwen, Creative Commons 4.0
Published February 22, 2024 by

Nonstop Flights: Seattle to/from Chicago $107-$123 r/t [March-April] – United / Alaska Airlines

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