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$67+ Cheap flights from Rhode Island to Chicago (CHI)

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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
PVD — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Rhode Island to Chicago

Keep the following information in mind while searching for Rhode Island to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$125
(Southwest)

One-way from

$67
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$199

Good round-trip deal

$303 or less

Good one-way deal

$154 or less
From Rhode Island to Chicago (CHI)
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One-way flight from Rhode Island to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Rhode Island to Chicago (CHI).
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Price to beat on a one-way flight from Rhode Island to Chicago (CHI).
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Find flight deals from Rhode Island to Chicago

Cheapest flights from Rhode Island to Chicago
Explore the most affordable flight options available from Rhode Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 10/285:15 amBOS - MDW
Nonstop2h 40mSouthwest
Tue 11/42:10 pmMDW - BOS
2 stops7h 05mSouthwest
Deal found 9/12$124
This Southwest deal was found by Cheapflights users on 9/12. 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 10/255:05 amBOS - MDW
2 stops8h 15mSouthwest
Mon 10/2711:25 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/12$125
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Tue 10/76:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/13$125
This Southwest deal was found by Cheapflights users on 9/12. 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 10/249:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Wed 10/2910:10 amMDW - BOS
2 stops8h 10mSouthwest
Deal found 9/12$126
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:16 amBOS - ORD
1 stop13h 22mSpirit Airlines
Tue 10/216:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/13$126
This Southwest deal was found by Cheapflights users on 9/14. 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 10/25:35 amBOS - MDW
1 stop5h 40mSouthwest
Mon 10/65:50 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/14$127
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:00 amBOS - ORD
Nonstop2h 56mJetBlue
Wed 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 9/13$127
This Southwest deal was found by Cheapflights users on 9/12. 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 10/45:20 amBOS - MDW
Nonstop2h 40mSouthwest
Tue 10/75:35 amMDW - BOS
1 stop4h 45mSouthwest
Deal found 9/12$129
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/153:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
Sat 10/1811:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Deal found 9/14$129
This Southwest deal was found by Cheapflights users on 9/12. 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 12/121:45 pmBOS - MDW
Nonstop2h 45mSouthwest
Sun 12/146:20 amMDW - BOS
1 stop5h 45mSouthwest
Deal found 9/12$131
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:38 amBOS - ORD
1 stop9h 07mMultiple Airlines
Tue 10/76:00 amORD - BOS
1 stop6h 20mMultiple Airlines
Deal found 9/14$131
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:00 amBOS - ORD
Nonstop2h 56mJetBlue
Wed 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 9/13$132

Cheapflights Fare Finder

 
Customize your flight search to find flights from Rhode Island to Chicago 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 September 15, 2025.
Use the filters below to find and compare flights from Rhode Island to Chicago that are best for you.

Fly from

Rhode Island

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 12/3

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Fri 12/5

6:20 am-11:45 am

1 stop4h 25m

$126

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/2

5:35 am-10:15 am

1 stop5h 40m

Chicago Midway

Mon 10/6

6:05 am-9:20 am

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/4

2:35 pm-4:15 pm

Nonstop2h 40m

Chicago Midway

Tue 10/7

5:35 am-12:50 pm

1 stop6h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 11/13

1:45 pm-3:30 pm

Nonstop2h 45m

Chicago Midway

Sun 11/16

5:00 am-12:50 pm

1 stop6h 50m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/30

10:05 am-2:10 pm

1 stop5h 05m

Chicago Midway

Mon 11/3

6:40 am-4:35 pm

1 stop8h 55m

$131

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 11/15

9:20 am-4:20 pm

1 stop8h 00m

Chicago Midway

Mon 11/17

11:25 am-9:40 pm

1 stop9h 15m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/10

9:30 am-11:34 am

Nonstop3h 04m

Chicago O'Hare Intl

Sat 1/10

4:15 pm-7:39 pm

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/26

3:17 pm-5:07 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sun 9/28

6:30 am-9:56 am

Nonstop2h 26m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/31

5:00 am-6:40 am

Nonstop2h 40m

Chicago Midway

Sun 11/2

5:45 am-5:10 pm

1 stop10h 25m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/25

8:35 am-10:10 am

Nonstop2h 35m

Chicago Midway

Sun 9/28

5:55 am-9:10 am

Nonstop2h 15m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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Best time to book a flight from Rhode Island to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Currently, August is the cheapest month in which you can book a flight from Rhode Island to Chicago (average of $245). Flying from Rhode Island to Chicago in March is currently the most expensive (average of $321). 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 CHI?

Find hourly flight availability from Rhode Island to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

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

Weekly flight availability from Rhode Island to Chicago

Explore weekly flight availability from Rhode Island to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from USRI to CHI are scheduled on a Monday (14 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (10 on average).

Related info for your journey

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

  • How long is the flight from Rhode Island to Chicago?

    Departing from Rhode Island to Chicago will take you 2h 56m. Rhode Island and Chicago are separated by a distance of 864 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Rhode Island to Chicago?

    The most popular flight routes from Rhode Island to Chicago are Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway and Providence-TFGreen - Chicago O'Hare Intl.

  • What are the most reliable airlines from Rhode Island to Chicago?

    Consider ANA (93%), Qatar Airways (91%) or Air Canada (77%) when booking your flight. These represent the most reliable airlines when flying from Rhode Island to Chicago.

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

    On average you can expect to pay $1,006 for a flight from Rhode Island to Chicago. The cheapest flight overall is $125 while the most popular route, (Boston Logan Intl - Chicago O'Hare Intl) is currently priced at $109.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Rhode Island to Chicago (average of $245). Flying from Rhode Island to Chicago in March is currently the most expensive (average of $321). 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?

Book flights to Chicago 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 Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Rhode Island to Chicago

Discover the top 4 airlines that operate flights from Rhode Island to Chicago. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$68Average$216FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$206Average$348FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$213Average$396FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$236Average$396FlexibilityNo cancel feeOn-time69%

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