Cheap flight from Houston to Chicago from $29

A nonstop flight from Houston to Chicago takes approximately 2.5 to 3 hours, and since Chicago is in the same time zone as Houston (both Central Time), there's no time change to adjust for. Be sure to get to the airport at least 2 hours early for your domestic flight.​

​​Leaving Houston:​​ Flights depart mainly from ​​George Bush Intercontinental Airport (IAH)​​ or ​​William P. Hobby Airport (HOU)​​. ​​Check your ticket carefully!​ These airports are 30–50+ minutes apart by car​​.

​​Arriving in Chicago:​​ You’ll land at ​​O'Hare International Airport (ORD)​​ or ​​Midway International Airport (MDW)​​. As the major international hub, ORD is ~17 miles NW of downtown, can be very busy. MDW is ~10 miles SW of downtown, and is often quicker to exit.

Airlines:​​ Major Carriers include United, American, Delta (mainly ORD), Southwest (both ORD & MDW from HOU). Most include a ​​free carry-on. For Low-Cost flights, try Spirit, Frontier (mainly ORD). Nonstop Tickets usually cost ​​~120–300.

​​Pro Tips:​​​​ IAH to ORD is most common for legacy carriers. HOU to MDW is Southwest's main route – often very efficient if it fits your needs.

Credit: Unsplash, Akshay Chauhan

Airports in Houston

Houston has 2 primary commercial airports:

• ​​George Bush Intercontinental Airport (IAH)​​ - Major international hub
• ​​William P. Hobby Airport (HOU)​​ - Mostly domestic/short-haul flights.

​​George Bush Intercontinental Airport (IAH)​

Located ​​23 miles north of downtown Houston​​, IAH handles ​​over 45 million passengers annually​​ as the city's primary international gateway.

Getting from Downtown to IAH​​

• METRORail + Bus: Take METRORail Red Line to downtown bus terminal, then Bus 102 (~$1.50, 75+ mins)
• Uber/Taxi: ~$40–70+ depending on traffic/time (40–70 mins)
• SuperShuttle: Shared vans ~$25–35 (book ahead)

​​William P. Hobby Airport (HOU)​

Situated ​​just 8 miles south of downtown Houston​​, HOU serves ​​more than 15 million passengers each year​​, primarily focusing on domestic and short-haul flights.

Getting from Downtown to HOU​​

• Bus 40: Direct route from Downtown Transit Center (~$1.50, 55+ mins)
• Uber/Taxi: ~$25–40 (20–30 mins with normal traffic)
• METRORail: Green Line to Magnolia Park Transit Center + Bus 88 (~$1.50, 50 mins)

Airports in Chicago

Chicago has 2 main airports:

• O'Hare International (ORD)​​ – Major global hub, one of the world's busiest.
• ​​Midway International (MDW)​​ – Primarily domestic/short-haul and low-cost carriers.
  

​​O'Hare International Airport (ORD)​​

Located ​​~17 miles northwest of downtown Chicago​​, ORD handles ​​over 70 million passengers annually​​ as the 3rd-busiest U.S. airport. Four terminals (1, 2, 3, 5) connected by the free ​​AirTrain​​ (operates 24/7 between terminals) and pedestrian walkways.

• ​​Getting from Downtown Chicago to ORD​​
• CTA Blue Line Train​​: Direct service from downtown stations. ​​($5 USD​​, ~45–55 mins).
• ​​Taxi/Uber/Lyft​​: ​​~45–75+​​depending on traffic ( 35–60mins).
• ​​Airport Shuttle (e.g., Go Airport Express)​​: ​​~$35–45 USD​​ shared ride (book online, travel time varies).

​​Midway International Airport (MDW)​​

Located ​​~11 miles southwest of downtown Chicago​​, MDW serves ​​around 20 million passengers annually​​, dominated by Southwest Airlines. One main terminal building divided into concourses (A, B, C) with short walking distances/gates.

​​Getting from Downtown Chicago to MDW​​

• ​​CTA Orange Line Train​​: Direct service from downtown stations. ​​($5 USD​​, ~25–35 mins).
• ​​Taxi/Uber/Lyft​​: ​​~35–50​​( 25–45mins).
• Airport Shuttle (e.g., Go Airport Express)​​: ​​~$25–35 USD​​ shared ride (book online).

Best Time to Fly to Chicago

Good months to fly are April-May or September-October. Weather's mild (10–20°C/50–70°F), crowds are manageable, and flights/hotels are moderately priced. ​​Summer (June-August)​​ is peak season—vibrant festivals (like Lollapalooza) and lake activities, but expect high prices, crowded attractions, and occasional heatwaves (up to 35°C/95°F). ​​Winter (December-February)​​ is brutally cold (-10–5°C/14–40°F) with heavy snow; flights face delays (ORD notorious for snow/fog), but you’ll find deep hotel discounts and ghost-town calm. Shoulder months (​​March​​ and ​​November​​) offer low prices but unpredictable rain/slush.

Hacks​​: Fly ​​Tue/Wed​​ for cheapest fares; avoid Friday/Sunday leisure travel. Book ​​3–4 months early​​ for summer deals or ​​last-minute​​ for winter steals. Nonstop flights from major hubs: NYC (~2.5–3 hrs), LA (~4 hrs), London (~8 hrs).

Credit: Unsplash

Where to Stay in Chicago

Book Chicago hotels on Trip.com! Most offer free cancellation for flexibility.

​​The Loop/River North​​: Downtown core – steps from Millennium Park, Art Institute, and Magnificent Mile shopping. Skyline views, luxury hotels, and easy transit access. Historic townhouses, chic boutiques, and quiet cafes. Mid-range to luxury boutique stays. Ideal for a relaxed but sophisticated vibe.
​​Wicker Park/Logan Square​​: Trendy, artistic neighborhoods with street art, vinyl record shops, and buzzing breweries. Great for longer stays or travelers seeking local immersion.

​​Pro Tips​​: Stay near an "L" train station​​ (especially Red/Blue Lines) – Chicago’s subway is the fastest way to beat traffic and reach attractions. ​​Noise-sensitive?​​ Skip neighborhoods near Wrigley Field (game nights get loud) or River North clubs.