Frontier has round-trip flights from Houston (IAH) to Chicago (ORD) for $56-$68, NONSTOP. Flights February to May. Weekends available. Origin/Destination reversible.
Category: <span>Chicago</span>
Image Credits: Daniel Schwen, Creative Commons 4.0
Image Credits: Daniel Schwen, Creative Commons 4.0
United and Southwest have round-trip flights from Houston (IAH/HOU) to Chicago, Memphis, Fort Lauderdale, or Orlando (ORD/MDW, MEM, FLL, MCO) for $97-$117, NONSTOP. Most flights January to March, except Memphis which had November to March. Weekends available. Origin/Destination reversible.
Memphis is the cheapest fare in this list, other destinations were about $117 round-trip.
Image Credits: Daniel Schwen, Creative Commons 4.0
Frontier has round-trip flights from Houston (IAH) to Chicago, Atlanta, Denver, Los Angeles, Miami, Orlando, or Tampa (ORD, ATL, DEN, LAX, MIA, MCO, TPA) for $39-$68, NONSTOP. $19-$34 each-way. Most flights are somewhere between September to November. Some weekends available. No Thanksgiving dates.
Image Credits: Daniel Schwen, Creative Commons 4.0
Frontier has round-trip flights from Houston (IAH) to Chicago (ORD) for $57, NONSTOP. Flights August to September. Departures on Monday and Thursday. Extended weekends available.
Image Credits: Daniel Schwen, Creative Commons 4.0
[06/09/2025 @ 10:20 AM CT] Price increased +$30.
American Airlines has round-trip flights from Houston (IAH) to Chicago (ORD) for $356, NONSTOP. Flights August to December. No Sunday departures. Very few weekends available. No Christmas dates available.
Image Credits: Daniel Schwen, Creative Commons 4.0
American Airlines, United, and Southwest have round-trip flights from Houston (IAH) to Chicago, Miami, Phoenix, or Los Angeles (ORD, MIA, PHX, LAX) for $121-$159, NONSTOP. Flights May to November. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.
Image Credits: Daniel Schwen, Creative Commons 4.0
Southwest has round-trip flights from Houston (HOU) to Chicago or Denver (MDW, DEN) for $138, NONSTOP. Flights September to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available. Origin/Destination reversible. No Christmas dates available.
Image Credits: Daniel Schwen, Creative Commons 4.0
Southwest has round-trip flights from Houston (HOU) to Chicago (MDW) for $113-$129, NONSTOP. Flights September to November. Very few weekends available. Origin/Destination reversible. No Thanksgiving dates.
Image Credits: Daniel Schwen, Creative Commons 4.0
American Airlines has round-trip flights from Houston (IAH) to Chicago, Miami, or Denver (ORD, MIA, DEN) for $139-$159, NONSTOP. Flights August to December. Mostly Tuesdays, Wednesdays, and Saturdays. Extended 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.
Image Credits: Daniel Schwen, Creative Commons 4.0
Southwest and American have round-trip flights from Houston (HOU/IAH) to Chicago, Fort Lauderdale, Miami, Denver, Tampa, or Orlando (MDW, FLL, MIA, DEN, TPA, MCO) for $92-$106, NONSTOP. Flights August to October. Extended weekends available. Origin/Destination reversible.
This is part of the Domestic Airfare sale that we mentioned a few days ago. There are more destinations on sale than this one that we are highlighting.
Image Credits: Daniel Schwen, Creative Commons 4.0
United and Southwest has round-trip flights from Houston (IAH) to Chicago, Fort Lauderdale, Nashville, Raleigh, Panama City, Florida, or Sacramento (ORD, FLL, BNA, RDU, ECP, SMF) for $117-$145, NONSTOP. Flights July to December. Some weekends available. Origin/Destination reversible. No Christmas dates available.
Note: Southwest is matching on some of these routes, but to get the discount requires jumping through a few annoying hoops. First, you can only see the fare in their slow and buggy Southwest App. Second, you have to use code “BDAY”.
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.
Image Credits: Daniel Schwen, Creative Commons 4.0
United has round-trip flights from Houston (IAH) to Chicago or Las Vegas (ORD, LAS) for $119-$128 / $157, NONSTOP. Flights July to November. Very few weekends available. Origin/Destination reversible. No Thanksgiving dates.
Las Vegas flights depart Tue, Wed, Sat.
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.
Image Credits: Kay Gaensler, Creative Commons 2.0 (flickr)
American Airlines and United have round-trip flights from Houston (IAH) to Chicago, Miami, Philadelphia, or Phoenix (ORD, MIA, PHL, PHX) for $139-$159, NONSTOP. Flights April to May. 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. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Daniel Schwen, Creative Commons 4.0
United and American Airlines have round-trip flights from Houston (IAH) to Chicago or Phoenix (ORD, PHX) for $139-$159, NONSTOP. Flights January 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.
Image Credits: Daniel Schwen, Creative Commons 4.0
American is matching (and beating) the Chicago fare that Southwest put on sale today. It was $155, now $118, same dates, give-or-take.
American Airlines has round-trip flights from Houston (IAH) to Chicago (ORD) for $118, NONSTOP. Flights September to February. Weekends available. Origin/Destination reversible.
Image Credits: Daniel Schwen, Creative Commons 4.0
American Airlines has round-trip flights from Houston (IAH) to Chicago (ORD) for $158-$161, NONSTOP. Flights March to May. Very few weekends available.
Image Credits: Daniel Schwen, Creative Commons 4.0
American Airlines and United have round-trip flights from Houston (IAH) to Chicago (ORD) for $138-$148, NONSTOP. Flights January to March. Extended weekends available. Origin/Destination reversible.
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
American Airlines, jetBlue, and United have round-trip flights from Houston (IAH) to Chicago or New York (ORD, LGA, JFK, EWR) for $138-$158, NONSTOP. Chicago flights December to March. New York flights from December to May and also September. 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.
Image Credits: Daniel Schwen, Creative Commons 4.0
American Airlines has round-trip flights from Houston (IAH) to Chicago (ORD) for $138-$158, NONSTOP. Flights November to March. Extended weekends available. Holiday blackouts. Cheapest flights are midweek.
Image Credits: Daniel Schwen, Creative Commons 4.0
American Airlines has round-trip flights from Houston (IAH) to Chicago (ORD) for $138-$158, NONSTOP. Flights September to December. Extended weekends available. Holiday blackouts.