CHI - HOU

$85 Find Cheap Flights from Chicago to Houston Hobby Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Hobby departing on 5/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Houston Hobby Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Houston, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Houston, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$169
Typical prices: $376-$197
Southwest
Wed 4/22Wed 4/22
MDW - HOU • Non-stop
Cheapest non-stop
$169
Typical prices: $377-$224
Southwest
Wed 4/29Wed 5/6
MDW - HOU • Non-stop
Top airlines
Cheapest • from $169 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 40m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
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Avoid delays
Most punctual • 81% on-time
Best time • Fewest delays
Insights
Insights
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When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 52% compared to booking last minute.
Insights
Insights
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Insights
When to travel
Cheapest • 20% price drop
Most popular
Good to know
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+1
+1
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We hope you love your trip to Hobby!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Hobby (CHI-HOU)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hobby that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Hobby

Wed, Apr 22 - Wed, Apr 22
Southwest Logo
7:25 am - 10:05 am
MDW
-
HOU
2h 40mnonstop
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
$169Southwest
Wed, Apr 22 - Wed, Apr 22
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
$175Southwest
Wed, Apr 22 - Thu, Apr 23
Southwest Logo
7:25 am - 10:05 am
MDW
-
HOU
2h 40mnonstop
Southwest Logo
5:10 am - 7:35 am
HOU
-
MDW
2h 25mnonstop
$184Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
2:40 pm - 7:55 pm
ORD
-
HOU
5h 15m
1 stop
Southwest Logo
6:40 am - 3:00 pm
HOU
-
ORD
8h 20m
1 stop
$189Southwest
Wed, Apr 29 - Thu, Apr 30
Southwest Logo
7:25 am - 10:05 am
MDW
-
HOU
2h 40mnonstop
Southwest Logo
4:25 pm - 8:25 pm
HOU
-
MDW
4h 00m
1 stop
$190Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
6:15 am - 6:15 pm
ORD
-
HOU
12h 00m
2 stops
Southwest Logo
6:00 am - 11:10 am
HOU
-
ORD
5h 10m
1 stop
$194Southwest
Wed, May 6 - Thu, May 7
Southwest Logo
12:15 pm - 2:55 pm
MDW
-
HOU
2h 40mnonstop
Southwest Logo
10:30 am - 2:55 pm
HOU
-
MDW
4h 25m
1 stop
$194Southwest
Wed, Apr 29 - Thu, Apr 30
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
Southwest Logo
4:25 pm - 8:25 pm
HOU
-
MDW
4h 00m
1 stop
$195Southwest
Tue, Apr 21 - Tue, Apr 28
Delta Logo
5:15 am - 12:40 pm
ORD
-
HOU
7h 25m
1 stop
Delta Logo
10:53 am - 4:42 pm
HOU
-
ORD
5h 49m
1 stop
$197Delta
Tue, Apr 21 - Tue, Apr 28
Delta Logo
10:41 am - 4:28 pm
MDW
-
HOU
5h 47m
1 stop
Delta Logo
10:53 am - 4:26 pm
HOU
-
MDW
5h 33m
1 stop
$197Delta
Booking Insights

KAYAK's insights & trends for Chicago to Hobby flights

Get data-powered insights and trends into flights from Chicago to Hobby to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Houston Hobby Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Houston Hobby Airport departing in April.

What is the cheapest Chicago to Houston Hobby Airport flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Houston Hobby Airport costs $246 on the route between Chicago Midway Airport (MDW) and Houston Hobby Airport (HOU). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Houston Hobby Airport?

The average price of all round-trip flights from Chicago to Houston Hobby Airport clicked on KAYAK for each day over the last 12 months.

For Chicago to Houston Hobby Airport, Thursday is the cheapest day to fly on average and Monday is the most expensive. Flying from Houston Hobby Airport back to Chicago, the best deals are generally found on Friday, with Monday being the most expensive.

What is the cheapest month to fly from Chicago to Houston Hobby Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Houston Hobby Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Houston Hobby Airport is September, where tickets cost $177 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $312 and $238 respectively.

Can I save money by flying with a layover from Chicago to Houston Hobby Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $227 on average.

How far in advance should I book a flight from Chicago to Houston Hobby Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Houston Hobby Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Houston Hobby Airport, you should book around 4 weeks before departure, which saves you about 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$85
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 40% increase in price.
Flight from Chicago Midway Airport to Houston Hobby Airport

When to book flights from Chicago to Hobby

Are your dates flexible? Find out the best times to travel from Chicago to Hobby based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Houston Hobby Airport flights

  • Which accommodation options are available at Hobby Airport?

    Located 1 mile away from the airport are luxurious hotels like the Days Inn & Suites, the DoubleTree by Hilton, Hampton Inn, and Holiday Inn, which provide cozy accommodations. The hotels also offer complimentary shuttles.

  • Does O'Hare Airport have disabled-friendly amenities?

    O'Hare Airport accommodates the needs of those with special needs and disabilities by providing amenities like elevators, Braille, accessible parking spots at lots B, C, D, F. G, H with ramps and elevators close by, operator-assisted phones in T2, T3, and T5, and mobility assistance.

  • What kind of public transportation can I use to get to Midway Airport from downtown Chicago?

    There is a regular and affordable train service—the Orange Line—that transports travelers from Downtown Chicago to MDW. Orange-Line trains take between 20min and 25min to complete the journey and charge around $2.50.

  • Does Midway Airport have lounges?

    Midway Airport has only one lounge, the USO lounge in Concourse C, which is open to those actively serving in the military and their families free of charge. The cozy lounge is equipped with gaming stations, a kitchenette with complimentary refreshments, TVs, and reading materials.

  • What is the cheapest flight from Chicago to Houston Hobby Airport?

    In the last 3 days, the lowest price for a flight from Chicago to Houston Hobby Airport was $85 for a one-way ticket and $169 for a round-trip.

  • Do I need a passport to fly between Chicago and Houston Hobby Airport?

    A passport is not required to fly from Chicago to Houston Hobby Airport.

  • Which airports will I be using when flying from Chicago to Houston Hobby Airport?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Houston Hobby.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Houston Hobby Airport?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago to Houston Hobby Airport flight route.

  • Which aircraft models fly most regularly from Chicago to Houston Hobby Airport?

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago to Houston Hobby Airport flight route.

  • Which airline alliances offer flights from Chicago to Houston Hobby Airport?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Houston Hobby Airport, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Houston Hobby Airport?

    There are nonstop flights from Chicago to Houston Hobby Airport on a daily basis.

  • Which is the best airline for flights from Chicago to Houston, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Southwest and United Airlines. With an average price for the route of $308 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $312 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Houston Hobby Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Houston Hobby Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Houston Hobby Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Houston Hobby Airport from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Houston Hobby Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Houston Hobby Airport with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Houston Hobby Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Houston Hobby Airport from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Houston Hobby Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $195 or less one-way and $336 or less round-trip.
  • Travelers can get nonstop flights to Hobby Airport (HOU) from Midway Airport (MDW) with Southwest Airlines. O'Hare Airport (ORD), which serves as a hub for United and American Airlines, also operates nonstop flights to Hobby Airport through both airlines.
  • O'Hare Airport provides tranquil spaces in their sophisticated lounges to ensure travelers get some much-needed relaxation time before their flights. The United Airlines United Club, located in Terminal 2, is one such lounge that one can access by paying around $59.
  • If you choose to drive yourself to Midway Airport, you can leave your vehicle at one of the long-term parking lots. The economy lot, which you will find on the northwest side of the terminal, provides convenient and affordable long-term parking at a rate of about $15. Free shuttles are available from the parking lot.
  • Hobby Airport provides families with essential amenities to ensure they have a stress-free time while at the airport. There is a children's play area in the west concourse. The airport also has two mothers'rooms situated right next to Gate 46 and Gate 4.
  • Travelers arriving at Hobby Airport can find Metro bus 40, which stops right outside the arrivals area. The Metro bus takes approximately 60min to travel from Hobby Airport to downtown Houston. The standard fare for the one-way trip is around $1.25.
  • Midway Airport has plenty of paintings, exhibits, sculptures, and murals spread all over the airport to give travelers a one-of-a-kind traveling experience. On the Mezzanine level of Midway Airport is the hanging sculpture that poetically links human-made and natural aviation.
  • Taking the GO Airport shuttle is a convenient way to travel from O'Hare Airport to downtown Chicago. Only passengers with one suitcase of standard size and one hand luggage are allowed onboard the shuttle. The standard fare for the shuttle trip, which takes approximately 45min, is around $30.

Prefer to fly direct from Chicago to Houston Hobby Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Houston Hobby.
Find which airlines fly direct from Chicago to Houston Hobby Airport, which days they fly and book direct flights.

Direct departures

Chicago to Houston Hobby

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Houston Hobby to Chicago

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 5 airlines serving from Chicago to Hobby

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Houston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Hobby? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4337 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Fine. The issues I had were associated with luggage being delayed from Turkey to Tanzania

We purchase first class seats for the first time for multiples of standard economy ticket. There was no access to the club lounge and no priority boarding. The meal and the service once on the plane were superior and the seat was nicer, but not worth the price difference. I will be happy to seat in economy and spend the difference on more travel.

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

Everything was on time and service on the flight was great!

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Very old flight - time to retire it for newer airplanes

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

flight delayed because of poor staffing and organization - confusion from gate agents and flight attendant supervisors scheduling a missing flight attendant. flight delay 1 hr 30 min

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Everything you need to know for your flight from Chicago to Hobby

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