Disclosure: Some links below are affiliate links. We may earn a commission at no extra cost to you. Learn more.
Expect to pay $120-$180 one-way for a basic economy ticket on a typical Chicago (ORD) to Houston (IAH) flight. I checked prices yesterday: United offered $159 for a midweek trip on September 15th. Booking last-minute usually means $250+.
Prices spike during Houston's rodeo season (late April) and Chicago's summer festivals. You'll pay $300+ for a last-minute seat on those dates. The cheapest month? October, when average prices dip to $110. Always check both airports – ORD is usually cheaper than MDW for this route.
Southwest Airlines wins for me. Their non-stop flights from Chicago Midway (MDW) to Houston Hobby (HOU) cost $130-$160 and include free checked bags. No change fees either – crucial if your Houston plans shift suddenly.
United and American are solid but pricey. United's $179 economy seats on a 3:15pm flight include a $30 bag fee. American's $185 tickets have a 30-inch seat pitch – cramped for a 3-hour flight. I avoid both for this route due to baggage fees and frequent delays. Delta doesn't fly this route directly.
Avoid Mondays and Fridays. Those are peak business travel days, pushing prices up 30%. Fly Tuesday or Wednesday instead – I booked a $120 United flight on a Tuesday last month.
Summer is expensive. July and August average $200+ one-way. The cheapest window is October to November. My friend flew to Houston for a conference in October for $115. Avoid Houston's Rodeo days – April 20-24, 2024, will cost you $250+.
Chicago's O'Hare (ORD) is the main hub – 95% of flights depart from there. But Midway (MDW) offers cheaper options. Southwest flies MDW to HOU, often $20 less than ORD flights. My rule: if your flight leaves before 7am, use MDW for the lower price.
Houston has two main airports: IAH (George Bush) and HOU (Hobby). IAH is bigger but 30 minutes from downtown. HOU is closer (15 minutes) and Southwest flies there exclusively. If you're going to the downtown area, HOU saves you $15-$20 on rideshares. IAH has more flight options but costs more in ground transport.
Book 5-6 weeks out. I've seen prices jump $50+ when I delayed booking. Use Google Flights' price tracking – set alerts for $130 and it notifies me when it drops. Last-minute deals rarely exist on this route.
Check baggage rules. Southwest includes two free bags; United charges $35 for the first bag. I always pack light for this route. Also, avoid flying through IAH for connections – the terminal transfer takes 45 minutes minimum. Fly direct whenever possible. A United connection through Denver added 2 hours to my trip last year.
A: Not really. St. Louis (STL) to Houston (IAH) is usually $10-$20 more than Chicago. You lose the direct flight advantage. Stick to Chicago airports for the best deals and options.
Which airport in Houston is better for downtown access?
Houston Hobby (HOU) is 15 minutes from downtown versus IAH's 30 minutes. Southwest's HOU flights are cheaper too. If you're only staying in the city center, HOU saves you time and money on taxis.
How early should I arrive at Chicago airports for this flight?
90 minutes minimum for domestic flights. I arrived 110 minutes early last week for a United flight and caught a delayed bus to my gate. 60 minutes is risky – security lines at ORD can be brutal, especially on Wednesday mornings.
A: Only with airlines like Southwest that offer full refunds. United and American rarely refund delays unless it's a massive 4+ hour wait. I always buy travel insurance for this route – $15 covers delays and missed connections on flights under $200.
✈️ Search Cheap Flights — Compare 728 airlines instantly
🏨 Find Hotels — Compare 100+ booking sites
🚗 Rent a Car — 800+ brands worldwide
🚙 Local Car Rental — Owner-operated fleets
🎧 Self-Guided Audio Tours
🎫 Skip-the-Line Tickets
🚕 Airport Transfer — Fixed price
🛡️ Travel Insurance from $4/day
📱 Get an eSIM — code FALLY20
✈️ Flight Delayed? Claim up to €600
Video by YouTube · For informational purposes only
© 2026 360 Business Tour · Privacy · Affiliate Disclosure
Related Reading
✈️ Compare Chicago To Houston Flights Prices | More Travel Guides