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Houston to Chicago flight ticket price

Compare live prices for HOU to MDW. Use the search panel to change origin, destination, passengers, cabin and trip type instantly.
HOU → MDW Approx. 1509.80 km 11 May 2026 Live inventory
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Showing 25 of 112 live flights
Spirit Airlines
NK-1015
07:15
05/11/2026
IAH
William P Hobby Airport
2h 39m
Non-stop
09:54
05/11/2026
ORD
Chicago Midway International Airport
₹6,801
per person
✕ Non-refundableLCC
Frontier Airlines
F9-1882
12:45
05/11/2026
IAH
William P Hobby Airport
2h 58m
Non-stop
15:43
05/11/2026
ORD
Chicago Midway International Airport
₹7,407
per person
✕ Non-refundable
Frontier Airlines
F9-4106
20:50
05/11/2026
IAH
William P Hobby Airport
11h 5m
1 Stop
⏱ ATL · 6h 26mATL Airport
07:55
05/12/2026
+1
ORD
Chicago Midway International Airport
₹7,591
per person
✕ Non-refundable
Delta Air Lines
DL-1389
05:20
05/11/2026
IAH
William P Hobby Airport
7h 41m
1 Stop
⏱ DTW · 3h 30mDTW Airport
13:01
05/11/2026
ORD
Chicago Midway International Airport
₹7,766
per person
✕ Non-refundable
Delta Air Lines
DL-1651
18:35
05/11/2026
IAH
William P Hobby Airport
5h 24m
1 Stop
⏱ ATL · 0h 52mATL Airport
23:59
05/11/2026
ORD
Chicago Midway International Airport
₹7,766
per person
✕ Non-refundable
Southwest Airlines
WN-3755
05:10
05/11/2026
HOU
William P Hobby Airport
2h 25m
Non-stop
07:35
05/11/2026
MDW
Chicago Midway International Airport
₹9,551
per person
✕ Non-refundable6 fare options
Spirit Airlines
NK-2803
16:20
05/11/2026
IAH
William P Hobby Airport
7h 36m
1 Stop
⏱ MIA · 1h 42mMIA Airport
23:56
05/11/2026
ORD
Chicago Midway International Airport
₹10,448
per person
✕ Non-refundable🔥 Last 4 seatsLCC
Spirit Airlines
NK-2438
09:58
05/11/2026
IAH
William P Hobby Airport
13h 17m
1 Stop
⏱ FLL · 7h 34mFLL Airport
23:15
05/11/2026
ORD
Chicago Midway International Airport
₹10,448
per person
✕ Non-refundableLCC
Southwest Airlines
WN-2443
19:20
05/11/2026
HOU
William P Hobby Airport
4h 10m
1 Stop
⏱ BNA · 0h 40mBNA Airport
23:30
05/11/2026
MDW
Chicago Midway International Airport
₹10,649
per person
✕ Non-refundable🔥 Last 4 seats6 fare options
Southwest Airlines
WN-50
18:30
05/11/2026
HOU
William P Hobby Airport
5h 25m
1 Stop
⏱ DAL · 1h 55mDAL Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹10,649
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-2403
21:50
05/11/2026
HOU
William P Hobby Airport
7h 10m
1 Stop
⏱ PHX · 1h 15mPHX Airport
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹10,649
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-46
17:30
05/11/2026
HOU
William P Hobby Airport
6h 25m
1 Stop
⏱ DAL · 3h 5mDAL Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹10,649
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-4
07:00
05/11/2026
HOU
William P Hobby Airport
7h 55m
1 Stop
⏱ DAL · 2h 50mDAL Airport
14:55
05/11/2026
MDW
Chicago Midway International Airport
₹11,149
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-46
17:30
05/11/2026
HOU
William P Hobby Airport
6h 0m
1 Stop
⏱ BNA · 0h 50mBNA Airport
23:30
05/11/2026
MDW
Chicago Midway International Airport
₹11,149
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-2422
07:35
05/11/2026
HOU
William P Hobby Airport
7h 20m
1 Stop
⏱ STL · 4h 10mSTL Airport
14:55
05/11/2026
MDW
Chicago Midway International Airport
₹11,177
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-40
16:00
05/11/2026
HOU
William P Hobby Airport
7h 55m
1 Stop
⏱ DAL · 4h 25mDAL Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹11,177
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-863
10:20
05/11/2026
HOU
William P Hobby Airport
9h 25m
1 Stop
⏱ SAV · 4h 55mSAV Airport
19:45
05/11/2026
MDW
Chicago Midway International Airport
₹11,177
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-2111
15:35
05/11/2026
HOU
William P Hobby Airport
7h 55m
2 Stops
⏱ VPS · 1h 0mVPS Airport⏱ BNA · 2h 5mBNA Airport
23:30
05/11/2026
MDW
Chicago Midway International Airport
₹11,182
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-40
16:00
05/11/2026
HOU
William P Hobby Airport
7h 30m
2 Stops
⏱ DAL · 2h 0mDAL Airport⏱ BNA · 0h 50mBNA Airport
23:30
05/11/2026
MDW
Chicago Midway International Airport
₹11,324
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-46
17:30
05/11/2026
HOU
William P Hobby Airport
6h 25m
2 Stops
⏱ DAL · 1h 5mDAL Airport⏱ AUS · 0h 45mAUS Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹11,324
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-40
16:00
05/11/2026
HOU
William P Hobby Airport
7h 55m
2 Stops
⏱ DAL · 2h 25mDAL Airport⏱ AUS · 0h 45mAUS Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹11,324
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-36
15:00
05/11/2026
HOU
William P Hobby Airport
8h 55m
2 Stops
⏱ DAL · 3h 30mDAL Airport⏱ AUS · 0h 45mAUS Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹11,324
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-36
15:00
05/11/2026
HOU
William P Hobby Airport
8h 40m
2 Stops
⏱ DAL · 1h 20mDAL Airport⏱ DEN · 1h 35mDEN Airport
23:40
05/11/2026
MDW
Chicago Midway International Airport
₹11,324
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-36
15:00
05/11/2026
HOU
William P Hobby Airport
8h 55m
2 Stops
⏱ DAL · 1h 30mDAL Airport⏱ AUS · 2h 40mAUS Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹11,324
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-2296
06:55
05/11/2026
HOU
William P Hobby Airport
8h 0m
2 Stops
⏱ BNA · 0h 45mBNA Airport⏱ SDF · 3h 0mSDF Airport
14:55
05/11/2026
MDW
Chicago Midway International Airport
₹11,324
per person
✕ Non-refundable4 fare options
😕 No flights match your filters.
Houston (HOU)
📍 William P Hobby Airport
🌍 United States
🕐 GMT -6
📐 Latitude: 29.64539909
📐 Longitude: -95.27890015
Chicago (MDW)
📍 Chicago Midway International Airport
🌍 United States
🕐 GMT -6
📐 Latitude: 41.785999
📐 Longitude: -87.752403

✈ Distance: Houston,USA to Chicago,USA1509.80 km

📅 Results on this page are loaded for 11 May 2026. Click View all flights for the complete live search.

Houston to Chicago — what to expect when booking

The HOU–MDW route is served by multiple carriers throughout the year. Fares on this route can move quickly — a price available now may not be there 30 minutes later.

If your dates are flexible, try shifting your departure by a day or two using the date strip above. Mid-week departures often show lower base fares compared to weekend starts on many routes.

The distance between Houston,USA and Chicago,USA is approximately 1509.80 km.

Before you book

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More flights from Houston (HOU)
43 routes
More flights from Chicago (MDW)
69 routes
Chicago Albany
MDW → ALB
Chicago Albuquerque
MDW → ABQ
Chicago Amarillo
MDW → AMA
Chicago Atlanta
MDW → ATL
Chicago Austin
MDW → AUS
Chicago Birmingham
MDW → BHM
Chicago Boston
MDW → BOS
Chicago Buffalo
MDW → BUF
Chicago Cancun
MDW → CUN
Chicago Charleston
MDW → CHS
Chicago Charlotte
MDW → CLT
Chicago Cleveland
MDW → CLE
Chicago Columbus
MDW → CMH
Chicago Denver
MDW → DEN
Chicago Des Moines
MDW → DSM
Chicago Detroit
MDW → DTW
Chicago Fort Lauderdale
MDW → FLL
Chicago Fort Myers
MDW → RSW
Chicago Greenville
MDW → GSP
Chicago Guadalajara
MDW → GDL
Chicago Hartford
MDW → BDL
Chicago Houston
MDW → HOU
Chicago Jackson
MDW → JAN
Chicago Jacksonville
MDW → JAX
Chicago Kansas City
MDW → MCI
Chicago Las Vegas
MDW → LAS
Chicago Leon
MDW → BJX
Chicago Little Rock
MDW → LIT
Chicago Los Angeles
MDW → LAX
Chicago Louisville
MDW → SDF
Chicago Manchester
MDW → MHT
Chicago Memphis
MDW → MEM
Chicago Minneapolis
MDW → MSP
Chicago Montego Bay
MDW → MBJ
Chicago Morelia
MDW → MLM
Chicago Nashville
MDW → BNA
Chicago New Orleans
MDW → MSY
Chicago New York
MDW → LGA
Chicago Norfolk
MDW → ORF
Chicago Oakland
MDW → OAK
Chicago Oklahoma City
MDW → OKC
Chicago Omaha
MDW → OMA
Chicago Ontario
MDW → ONT
Chicago Orlando
MDW → MCO
Chicago Philadelphia
MDW → PHL
Chicago Phoenix
MDW → PHX
Chicago Pittsburgh International Airport
MDW → PIT
Chicago Portland International
MDW → PDX
Chicago Providence
MDW → PVD
Chicago Punta Cana
MDW → PUJ
Chicago Raleigh
MDW → RDU
Chicago Reno
MDW → RNO
Chicago Rochester
MDW → ROC
Chicago Sacramento
MDW → SMF
Chicago Salt Lake City
MDW → SLC
Chicago San Antonio
MDW → SAT
Chicago San Diego
MDW → SAN
Chicago San Francisco
MDW → SFO
Chicago San Jose
MDW → SJC
Chicago Seattle
MDW → SEA
Chicago St. Louis
MDW → STL
Chicago Tampa
MDW → TPA
Chicago Toronto
MDW → YTZ
Chicago Trenton
MDW → TTN
Chicago Tucson
MDW → TUS
Chicago Tulsa
MDW → TUL
Chicago Washington DC
MDW → IAD
Chicago Wichita
MDW → ICT
Chicago Zacatecas
MDW → ZCL
❓ Frequently asked questions — Houston to Chicago flights

Generally yes — fares on most routes are most competitive around 4–6 weeks before departure. Booking earlier usually means better availability and a lower base fare when your dates are fixed.

The straight-line distance between Houston,USA (HOU) and Chicago,USA (MDW) is approximately 1509.80 km. Actual flying distance may vary slightly depending on routing.

Non-stop availability on this route varies by airline schedule and season. Use the filters below to quickly check whether direct options are available on your selected date.

Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.