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Flights from Houston to Chicago from $63

Book your flight from Houston (HOU) to Chicago (MDW) at the best prices. Fares start from $389.
Houston

HOU

→

Chicago

MDW

11/24/2025 – 12/01/2025

Cheap flight deals from Houston to Chicago

Average price start from:
i

$130

Round-trip flights from Houston to Chicago starting at $130. Book now for the best deals!

One-way from:
i

$63

One-way flights from Houston to Chicago starting at $63. Great for flexible travel!

Cheapest day:
i

Wednesday

Wednesday is the cheapest day to fly from Houston to Chicago. Save more by booking on this day!

Cheapest In:
i

$113

Sep 2025

Sep 2025 is the cheapest month to fly from Houston to Chicago with prices starting at $113.

Find flight deals from Houston to Chicago

Cheapest flights from Houston to Chicago

ONEWAY FLIGHTS

LAST MINUTE

CHEAP FLIGHTS

BEST FLIGHTS

Explore the cheapest oneway flights from Houston to Chicago spotted daily.

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

MDW

Unknown City

$63

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

ORD

Unknown City

$63

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

MDW

Unknown City

$70

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

IND

Unknown City

$85

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

ORD

Unknown City

$109

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

MDW

Unknown City

$120

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

MDW

Unknown City

$129

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

ORD

Unknown City

$129

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

ORD

Unknown City

$130

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

SDF

Unknown City

$131

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

ORD

Unknown City

$140

Non-stop • 60 min

HOU

Houston

HOU - Houston • 2025-11-24 • 09:00

Unknown

60 min

SDF

Unknown City

$141

Non-stop • 60 min

Price Trends & Analysis

Weekly Price Trends

If your flying dates are flexible, consider flying to Chicago on a Wednesday.

Monthly Price Trends

Lowest fares from Houston to Chicago typically available in April.

Weather & Climate Information

Temperature

Chicago experiences a humid continental climate, with cold winters averaging temperatures between 20°F to 30°F and hot summers ranging from 70°F to 90°F. The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and precipitation is generally lower.

Rainfall

The best time to visit Chicago is during late spring (May to early June) or early fall (September to October) when the weather is mild and pleasant. These seasons also feature vibrant local events like the Chicago Blues Festival and the Chicago Gourmet, ensuring a lively atmosphere without the summer tourist crowds.

Airlines at MDW

Experience seamless travel from Houston to Chicago with trusted airlines like Frontier Airlines, Southwest Airlines, Delta Air Lines, American Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers. Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Houston to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.

Places to Visit in Chicago

Chicago, the Windy City, captivates with its stunning skyline adorned by architectural marvels like the Willis Tower and the historic Tribune Tower. Rich in cultural heritage, visitors can explore world-class museums like the Art Institute, savor deep-dish pizza, and stroll through the vibrant neighborhoods that pulse with music and art. Experience the lively atmosphere of Millennium Park, where public art meets lush green spaces, and immerse yourself in the city’s dynamic spirit that celebrates both its storied past and innovative future.

About Chicago

Discover the beauty of Chicago when flying from Houston. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.

Airlines Flying from Houston to Chicago

Experience seamless travel from Houston to Chicago with trusted airlines like Frontier Airlines, Southwest Airlines, Delta Air Lines, American Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers. Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Houston to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.

Hotels in Chicago

Explore excellent hotel options near MDW Airport for your Chicago visit. These hotels near Chicago airport combine convenience with comfort, making them perfect for both short layovers and extended stays. Check for special offers and airport shuttle services.
Hotel

Hotel

Category: Standard

Comfortable accommodations with modern amenities.

Location: Near airport

Hotel ID:

About Chicago

Discover the beauty of Chicago when flying from Houston. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.

Places to Visit in Chicago

Chicago, the Windy City, captivates with its stunning skyline adorned by architectural marvels like the Willis Tower and the historic Tribune Tower. Rich in cultural heritage, visitors can explore world-class museums like the Art Institute, savor deep-dish pizza, and stroll through the vibrant neighborhoods that pulse with music and art. Experience the lively atmosphere of Millennium Park, where public art meets lush green spaces, and immerse yourself in the city’s dynamic spirit that celebrates both its storied past and innovative future.

Hotels in Chicago

Explore excellent hotel options near MDW Airport for your Chicago visit. These hotels near Chicago airport combine convenience with comfort, making them perfect for both short layovers and extended stays. Check for special offers and airport shuttle services.
Hotel

Hotel

Category: Standard

Comfortable accommodations with modern amenities.

Location: Near airport

Hotel ID:

Airlines Flying from Houston to Chicago

Experience seamless travel from Houston to Chicago with trusted airlines like Frontier Airlines, Southwest Airlines, Delta Air Lines, American Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers. Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Houston to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.

Frequently Asked Questions

How much does it cost to fly from Houston to Chicago?

Flight prices start from $63 for this route. Save more by booking during April and choosing Wednesday departures.

What's the flight duration from Houston to Chicago?

The typical flight time is approximately 10-15 hours, with most routes featuring one stopover for better pricing and convenience.

What airlines serve the Houston to Chicago route?

Several airlines operate flights including Frontier Airlines, Southwest Airlines, Delta Air Lines. Compare schedules and prices to find the best option for your travel needs.

When should I book my flight for the best price?

For optimal savings, book 2-3 months ahead and consider traveling during April when demand is lower.

Where can I stay near MDW Airport?

There are several hotels near MDW Airport with convenient shuttle services. Many offer comfortable accommodations for both business and leisure travelers.

What makes Chicago worth visiting?

Chicago combines rich cultural heritage with modern attractions. Visit during pleasant weather months to experience the city at its best.

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