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$107+ Cheap flights from Chicago (CHI) to Gulfport (GPT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Find cheap flights from Chicago to Gulfport with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheap flight deals from Chicago to Gulfport

Best flights from Chicago to Gulfport
Discover carefully curated flight deals from Chicago to Gulfport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 2, 2026.

This Delta deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/3010:48 amMDW - GPT
1 stop6h 27mDelta
Tue 2/310:21 amGPT - MDW
1 stop7h 08mDelta
Deal found 1/1$269
This American Airlines deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/283:23 pmORD - GPT
1 stop8h 10mAmerican Airlines
Sun 2/15:29 pmGPT - ORD
1 stop5h 58mAmerican Airlines
Deal found 12/31$269
This United Airlines deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1410:35 amORD - GPT
1 stop5h 26mUnited Airlines
Wed 2/184:55 pmGPT - ORD
1 stop7h 31mUnited Airlines
Deal found 1/1$326
This Delta deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/244:30 pmMDW - GPT
1 stop5h 23mDelta
Sat 1/3110:21 amGPT - MDW
1 stop5h 17mDelta
Deal found 1/1$269
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/610:48 amMDW - GPT
1 stop6h 27mDelta
Mon 2/96:08 pmGPT - MDW
1 stop4h 14mDelta
Deal found 12/31$269
This American Airlines deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/104:04 pmORD - GPT
2 stops7h 45mAmerican Airlines
Sat 3/141:04 pmGPT - ORD
1 stop6h 36mAmerican Airlines
Deal found 12/31$299
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:50 amORD - GPT
1 stop4h 09mDelta
Sat 3/143:00 pmGPT - ORD
1 stop5h 02mDelta
Deal found 12/31$269
This United Airlines deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/97:35 amORD - GPT
1 stop8h 23mUnited Airlines
Mon 1/125:13 pmGPT - ORD
1 stop5h 45mUnited Airlines
Deal found 12/30$339
This American Airlines deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/63:23 pmORD - GPT
1 stop8h 10mAmerican Airlines
Sat 1/171:45 pmGPT - ORD
2 stops8h 49mAmerican Airlines
Deal found 1/1$330
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/149:55 amORD - GPT
1 stop5h 14mDelta
Sat 1/1710:21 amGPT - ORD
1 stop6h 23mDelta
Deal found 12/31$279
This United Airlines deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/207:35 amORD - GPT
1 stop6h 32mUnited Airlines
Sat 1/245:13 pmGPT - ORD
1 stop7h 15mUnited Airlines
Deal found 12/30$373
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:40 pmMDW - GPT
1 stop4h 35mDelta
Sun 3/225:57 pmGPT - MDW
1 stop4h 34mDelta
Deal found 12/31$294
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/102:50 pmORD - GPT
1 stop7h 03mDelta
Tue 2/1710:11 amGPT - ORD
1 stop6h 38mDelta
Deal found 12/31$294
This Delta deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:05 amORD - GPT
1 stop6h 46mDelta
Sun 2/86:05 amGPT - ORD
1 stop7h 35mDelta
Deal found 1/1$294
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/145:25 amORD - GPT
1 stop4h 15mDelta
Tue 2/1710:11 amGPT - ORD
1 stop6h 38mDelta
Deal found 12/31$294
This Delta deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/62:50 pmORD - GPT
1 stop7h 03mDelta
Sat 1/1710:21 amGPT - ORD
1 stop6h 23mDelta
Deal found 1/1$324
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1010:45 amMDW - GPT
1 stop6h 26mDelta
Sat 3/149:48 amGPT - MDW
1 stop5h 37mDelta
Deal found 12/31$368
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/145:31 pmMDW - GPT
1 stop4h 22mDelta
Sat 1/1710:21 amGPT - MDW
1 stop6h 08mDelta
Deal found 12/31$409
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/144:13 pmMDW - GPT
1 stop5h 41mDelta
Tue 2/176:00 amGPT - MDW
1 stop5h 59mDelta
Deal found 12/31$519
This Delta deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/284:30 pmMDW - GPT
1 stop5h 45mDelta
Fri 4/36:00 amGPT - MDW
1 stop6h 02mDelta
Deal found 1/1$524
This Delta deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/284:30 pmMDW - GPT
1 stop5h 45mDelta
Sat 4/49:48 amGPT - MDW
1 stop5h 37mDelta
Deal found 1/1$524
This Delta deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:45 pmMDW - GPT
1 stop4h 30mDelta
Sun 2/156:00 amGPT - MDW
1 stop4h 06mDelta
Deal found 1/1$539
This Delta deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2710:49 amMDW - GPT
1 stop6h 26mDelta
Mon 3/26:00 pmGPT - MDW
1 stop4h 31mDelta
Deal found 12/31$629
This Delta deal was found by Cheapflights users on 1/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/165:31 pmMDW - GPT
1 stop4h 22mDelta
Tue 1/206:05 amGPT - MDW
1 stop5h 54mDelta
Deal found 1/1$639

Find flight deals from Chicago to Gulfport

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Gulfport (GPT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Delta)

One-way from

$107
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$442
Provider with most accurate pricing for Chicago (CHI)-Gulfport Biloxi Regional flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Gulfport Biloxi Regional flights.
Search Deals
From Chicago (CHI) to Gulfport Biloxi Regional
Search Deals
One-way flight from Chicago (CHI) to Gulfport Biloxi Regional
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Gulfport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 2, 2026.
Use the filters below to find and compare flights from Chicago to Gulfport that are best for you.

Fly from

Chicago

Fly to

Gulfport

Route

Depart

Return

Price

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 1/30

10:48 am-5:15 pm

1 stop6h 27m

Gulfport Biloxi Regional

Tue 2/3

10:21 am-5:29 pm

1 stop7h 08m

$269

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/28

3:23 pm-11:33 pm

1 stop8h 10m

Gulfport Biloxi Regional

Sun 2/1

5:29 pm-11:27 pm

1 stop5h 58m

$269

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 1/24

4:30 pm-9:53 pm

1 stop5h 23m

Gulfport Biloxi Regional

Sat 1/31

10:21 am-3:38 pm

1 stop5h 17m

$269

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 2/6

10:48 am-5:15 pm

1 stop6h 27m

Gulfport Biloxi Regional

Mon 2/9

6:08 pm-10:22 pm

1 stop4h 14m

$269

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 3/10

9:50 am-1:59 pm

1 stop4h 09m

Gulfport Biloxi Regional

Sat 3/14

3:00 pm-8:02 pm

1 stop5h 02m

$269

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/14

9:55 am-3:09 pm

1 stop5h 14m

Gulfport Biloxi Regional

Sat 1/17

10:21 am-4:44 pm

1 stop6h 23m

$279

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 3/18

5:40 pm-10:15 pm

1 stop4h 35m

Gulfport Biloxi Regional

Sun 3/22

5:57 pm-10:31 pm

1 stop4h 34m

$294

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 2/10

2:50 pm-9:53 pm

1 stop7h 03m

Gulfport Biloxi Regional

Tue 2/17

10:11 am-4:49 pm

1 stop6h 38m

$294

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 2/6

7:05 am-1:51 pm

1 stop6h 46m

Gulfport Biloxi Regional

Sun 2/8

6:05 am-1:40 pm

1 stop7h 35m

$294

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 2/14

5:25 am-9:40 am

1 stop4h 15m

Gulfport Biloxi Regional

Tue 2/17

10:11 am-4:49 pm

1 stop6h 38m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 33 results
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Compare providers for flights from Chicago to Gulfport

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Gulfport in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Gulfport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Gulfport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Gulfport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Gulfport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Gulfport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Gulfport

Have a flexible travel schedule? Discover the best time to fly to Gulfport from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Gulfport

What is the cheapest month to book a flight from Chicago to Gulfport?

Currently, June is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $80). Flying from Chicago to Gulfport in July is currently the most expensive (average of $161). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Chicago to Gulfport?

How often are flights from Chicago to Gulfport delayed?

About 39% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 92 minutes.

What is the most punctual flight time for Chicago to Gulfport flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Monday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Gulfport flights?

Over the last year, Sun Country Air have had the lowest number of delays on this route, with just 50% of flights being delayed.

Reviews of airlines servicing Gulfport

Get insights into the airlines that provide service to Gulfport. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Gulfport. Reviews last updated January 2, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chicago to Gulfport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,021 reviews

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,021 reviews
Delta
7.9
Good
8,021 reviews

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,132 reviews
Delta
7.9
Good
8,021 reviews

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,074 reviews
Delta
7.9
Good
8,021 reviews

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Gulfport. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Gulfport from Chicago?

    Gulfport Biloxi Regional (GPT), located 3.1 mi from the city center, is the airport you fly into when you book flights from Chicago to Gulfport. 2 airlines have flights to Biloxi Regional from Chicago on a regular basis. Booking flights from Chicago to Gulfport Biloxi Regional should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Gulfport?

    Delta and American Airlines can get you from Chicago to Gulfport in just under 6h 27m. Your travel time can differ by up to 1h 43m. The distance from Chicago to Gulfport is about 789 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Gulfport round-trip?

    Flying on American Airlines is currently your cheapest option to Gulfport, with prices starting at $248. Another option worth looking into is Delta, starting at $248 round trip. You may be able to fly from Chicago to Gulfport for 41% less than the average price by searching for these airlines.

  • Can I find deals for flights from Chicago to Gulfport that include hotel bookings?

    Yes. In addition to deals on Chicago to Gulfport flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Gulfport?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Gulfport.

  • Can I find deals for business class flights from Chicago to Gulfport?

    Yes. Cheapflights offers flight deals from Chicago to Gulfport by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Gulfport?

    Currently, June is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $80). Flying from Chicago to Gulfport in July is currently the most expensive (average of $161). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Gulfport?

Book flights to Gulfport if you plan to visit one of these locations
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Alternative routes for Chicago to Gulfport

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Top 2 airlines flying from Chicago to Gulfport

Discover the top 2 airlines that operate flights from Chicago to Gulfport. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$336FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$392FlexibilityNo cancel feeOn-timeN/A

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