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$59+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
PVD — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This Southwest deal was found by Cheapflights users on 11/5. 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 12/55:30 amBOS - MDW
Nonstop2h 45mSouthwest
Mon 12/86:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 11/5$117
This Delta deal was found by Cheapflights users on 11/6. 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 12/127:52 pmBOS - ORD
Nonstop2h 55mDelta
Sun 12/147:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 11/6$117
This Southwest deal was found by Cheapflights users on 11/6. 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.
Sun 12/76:55 pmBOS - MDW
Nonstop2h 50mSouthwest
Tue 12/912:55 pmMDW - BOS
1 stop7h 10mSouthwest
Deal found 11/6$118
This American Airlines deal was found by Cheapflights users on 11/5. 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 11/127:19 pmBOS - ORD
Nonstop3h 06mAmerican Airlines
Wed 12/38:40 pmORD - BOS
Nonstop2h 33mAmerican Airlines
Deal found 11/5$118
This Kissandfly.com deal was found by Cheapflights users on 11/6. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:30 amBOS - ORD
Nonstop3h 05mJetBlue
Wed 12/177:00 amORD - BOS
1 stop7h 14mJetBlue
Deal found 11/6$119
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 12/1111:28 amBOS - ORD
1 stop6h 59mFrontier
Thu 12/256:00 amORD - BOS
1 stop18h 19mFrontier
Deal found 11/5$120
This Southwest deal was found by Cheapflights users on 11/5. 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 12/45:30 amBOS - MDW
Nonstop2h 45mSouthwest
Mon 12/86:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 11/5$122
This JetBlue deal was found by Cheapflights users on 11/6. 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.
Thu 12/45:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 11/6$122
This Southwest deal was found by Cheapflights users on 11/5. 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 12/27:45 amBOS - MDW
2 stops6h 15mSouthwest
Wed 12/36:20 amMDW - BOS
1 stop4h 25mSouthwest
Deal found 11/5$124
This Delta deal was found by Cheapflights users on 11/6. 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 12/127:52 pmBOS - ORD
Nonstop2h 55mDelta
Fri 12/197:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 11/6$124
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:30 amBOS - ORD
Nonstop3h 05mJetBlue
Tue 12/1611:25 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 11/6$125
This JetBlue deal was found by Cheapflights users on 11/6. 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.
Sat 12/63:40 pmBOS - ORD
1 stop7h 12mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 11/6$126

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 November 6, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

April

Cheapest in

September

Average price

$248

Good round-trip deal

$343 or less

Good one-way deal

$198 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Rhode Island to Chicago (CHI)
Search Deals
One-way flight from Rhode Island to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Rhode Island to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Rhode Island to Chicago (CHI).
Search Deals

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 November 6, 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 12/10

8:30 am-12:45 pm

1 stop5h 15m

Chicago Midway

Fri 12/12

7:15 pm-10:30 pm

Nonstop2h 15m

$118

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/12

6:50 pm-11:30 pm

1 stop5h 40m

Chicago Midway

Mon 12/15

6:15 pm-9:35 pm

Nonstop2h 20m

$118

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/11

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Fri 12/26

7:41 pm-11:10 pm

Nonstop2h 29m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 12/6

3:40 pm-9:52 pm

1 stop7h 12m

Chicago O'Hare Intl

Mon 12/8

8:38 pm-12:06 am

Nonstop2h 28m

$126

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/5

6:00 pm-10:35 pm

1 stop5h 35m

Chicago Midway

Sun 12/7

7:15 pm-10:30 pm

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 11/21

5:00 am-12:15 pm

1 stop8h 15m

Chicago O'Hare Intl

Tue 12/2

1:45 pm-10:15 pm

1 stop7h 30m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/9

9:40 am-11:40 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 12/22

9:12 pm-12:45 am

Nonstop2h 33m

$136

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

9:00 am-12:34 pm

1 stop4h 34m

Chicago Midway

Mon 12/15

1:14 pm-8:00 pm

1 stop5h 46m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 11/19

1:35 pm-3:20 pm

Nonstop2h 45m

Chicago Midway

Thu 11/20

12:55 pm-9:05 pm

1 stop7h 10m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/5

6:00 pm-10:35 pm

1 stop5h 35m

Chicago Midway

Tue 12/9

5:35 am-1:30 pm

1 stop6h 55m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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, February is the cheapest month in which you can book a flight from Rhode Island to Chicago (average of $130). Flying from Rhode Island to Chicago in March is currently the most expensive (average of $285). 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 November 6, 2025.

When flying from Rhode Island to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 8% versus a flight in the evening.

What is the cheapest day to fly from Rhode Island to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Rhode Island to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Rhode Island to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 6, 2025.

The most flights from USRI to CHI are scheduled on a Thursday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 3h. Rhode Island and Chicago are separated by a distance of 864 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Delta and United Airlines, as they are both options that can get you from Rhode Island to Chicago for a low price.

  • 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 (87%), United Airlines (87%) or Republic Airways (83%) 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 $712 for a flight from Rhode Island to Chicago. The cheapest flight overall is $139 while the most popular route, (Boston Logan Intl - Chicago O'Hare Intl) is currently priced at $99.

  • 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, February is the cheapest month in which you can book a flight from Rhode Island to Chicago (average of $130). Flying from Rhode Island to Chicago in March is currently the most expensive (average of $285). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$68Average$216FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$220Average$394FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$230Average$358FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$253Average$398FlexibilityNo cancel feeOn-time69%

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