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$69+ Cheap flights from Rhode Island to Midway (MDW)

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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
PVD — MDW
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheap flight deals from Rhode Island to Midway

Keep the following information in mind while searching for Rhode Island to Midway flight deals. Data was last updated August 13, 2025.

Round-trip from

$158
(Southwest)

One-way from

$69
(Southwest)

Popular in

March

Cheapest in

September

Average price

$223

Good round-trip deal

$280 or less

Good one-way deal

$179 or less
From Rhode Island to Chicago Midway
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One-way flight from Rhode Island to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Rhode Island to Chicago Midway.
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Price to beat on a one-way flight from Rhode Island to Chicago Midway.
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Find flight deals from Rhode Island to Midway

Cheapest flights from Rhode Island to Midway
Explore the most affordable flight options available from Rhode Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:55 pmBOS - MDW
Nonstop2h 50mSouthwest
Sun 11/169:35 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 8/11$158
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/410:45 amBOS - MDW
1 stop5h 05mSouthwest
Sun 9/75:55 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 8/12$168
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:35 amBOS - MDW
2 stops8h 35mSouthwest
Mon 9/86:45 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 8/12$173
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:15 amBOS - MDW
Nonstop2h 45mSouthwest
Mon 11/109:05 pmMDW - BOS
1 stop10h 10mSouthwest
Deal found 8/12$174
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/196:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 8/12$177
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/275:20 amBOS - MDW
1 stop4h 15mSouthwest
Wed 10/18:35 amMDW - BOS
1 stop5h 50mSouthwest
Deal found 8/12$178
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:35 pmBOS - MDW
1 stop4h 30mSouthwest
Tue 12/92:30 pmMDW - BOS
2 stops6h 45mSouthwest
Deal found 8/11$179
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:15 amBOS - MDW
Nonstop2h 30mSouthwest
Mon 8/252:35 pmMDW - BOS
1 stop7h 25mSouthwest
Deal found 8/11$187
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:15 amBOS - MDW
Nonstop2h 45mSouthwest
Sun 11/96:20 amMDW - BOS
1 stop5h 45mSouthwest
Deal found 8/12$188
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:40 amBOS - MDW
2 stops8h 45mSouthwest
Wed 9/106:25 amMDW - BOS
1 stop8h 00mSouthwest
Deal found 8/11$189
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:45 pmPVD - MDW
Nonstop2h 35mSouthwest
Sat 10/185:45 pmMDW - PVD
Nonstop2h 10mSouthwest
Deal found 8/13$203
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:35 amPVD - MDW
1 stop4h 25mSouthwest
Tue 9/161:00 pmMDW - PVD
Nonstop2h 15mSouthwest
Deal found 8/12$213

Cheapflights Fare Finder

 
Customize your flight search to find flights from Rhode Island to Midway 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 August 13, 2025.
Use the filters below to find and compare flights from Rhode Island to Chicago Midway Airport that are best for you.

Fly from

Rhode Island

Fly to

Midway

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/11

8:20 pm-9:55 pm

Nonstop2h 35m

Chicago Midway

Sun 9/14

5:55 am-9:10 am

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 9/10

9:25 am-11:05 am

Nonstop2h 40m

Chicago Midway

Fri 9/12

6:45 pm-10:05 pm

Nonstop2h 20m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 8/29

8:20 pm-9:55 pm

Nonstop2h 35m

Chicago Midway

Mon 9/8

6:45 am-10:00 am

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 9/13

5:50 am-7:25 am

Nonstop2h 35m

Chicago Midway

Sun 9/14

5:55 am-9:10 am

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 9/10

3:15 pm-4:50 pm

Nonstop2h 35m

Chicago Midway

Sun 9/14

5:55 am-9:10 am

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 9/16

3:15 pm-4:50 pm

Nonstop2h 35m

Chicago Midway

Fri 9/19

6:45 pm-10:05 pm

Nonstop2h 20m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/8

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Sun 10/12

6:05 am-9:20 am

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/8

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Tue 10/14

6:05 am-9:20 am

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/3

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Sun 10/12

6:05 am-9:20 am

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/11

8:20 pm-9:55 pm

Nonstop2h 35m

Chicago Midway

Fri 9/12

6:45 pm-10:05 pm

Nonstop2h 20m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 35 results
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Best time to book a flight from Rhode Island to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Rhode Island 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 Rhode Island to Chicago Midway Airport

What is the cheapest month to book a flight from Rhode Island to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Rhode Island to Chicago Midway Airport (average of $160). Flying from Rhode Island to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

What is the cheapest time of day to fly from RI to MDW?

Find hourly flight availability from Rhode Island to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 13, 2025.

When flying from Rhode Island to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

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

  • What are the cheapest airlines to fly from Rhode Island to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $69 on Southwest. Other airlines that offer cheap prices include Delta from $109 and Frontier from $109 one-way.

  • What are the cheapest flights from Rhode Island to Chicago Midway Airport?

    While on average a flight from Rhode Island to Chicago Midway Airport is generally $300, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $99 for that flight.

  • Can I find deals for flights from Rhode Island to Midway that include hotel bookings?

    Yes. In addition to deals on Rhode Island to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Rhode Island to Midway?

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

  • Can I find deals for business class flights from Rhode Island to Midway?

    Yes. Cheapflights offers flight deals from Rhode Island to Midway 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 Rhode Island to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Rhode Island to Chicago Midway Airport (average of $160). Flying from Rhode Island to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Rhode Island to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Rhode Island to Midway

Discover the top 2 airlines that operate flights from Rhode Island to Midway. 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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$204Average$346FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$232Average$434FlexibilityNo cancel feeOn-time71%

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