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$98+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
PVD — CHI
Aug 5 — Aug 121
Wed 8/5
Wed 8/12
1 adult, Economy
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Cheap 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 July 6, 2026.

This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:20 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Mon 7/277:35 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 7/1$170
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 7/1512:01 pm
BOS
-
ORD
Nonstop3h 01m
American Airlines
Wed 7/226:00 am
ORD
-
BOS
Nonstop2h 34m
American Airlines
Deal found 7/1$170
This Southwest deal was found by Cheapflights users on 7/6. 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.
Sat 8/225:30 am
BOS
-
MDW
1 stop5h 00m
Southwest
Sat 8/293:10 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 7/6$172
This United Airlines deal was found by Cheapflights users on 7/3. 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 7/258:20 pm
BOS
-
ORD
Nonstop3h 00m
United Airlines
Tue 7/286:00 am
ORD
-
BOS
1 stop4h 16m
United Airlines
Deal found 7/3$172
This Southwest deal was found by Cheapflights users on 7/2. 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 8/257:15 pm
BOS
-
MDW
Nonstop2h 35m
Southwest
Wed 9/96:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 7/2$173
This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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.
Thu 9/38:15 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Wed 9/99:38 am
ORD
-
BOS
Nonstop2h 28m
JetBlue
Deal found 7/3$173
This Flysmarter deal was found by Cheapflights users on 7/2. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:41 am
BOS
-
ORD
1 stop8h 36m
JetBlue
Mon 8/248:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Deal found 7/2$174
This Southwest deal was found by Cheapflights users on 7/3. 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 7/255:20 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Sat 7/255:45 pm
MDW
-
BOS
Nonstop2h 25m
Southwest
Deal found 7/3$175
This JetBlue deal was found by Cheapflights users on 7/2. 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.
Wed 8/128:15 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Thu 8/209:35 am
ORD
-
BOS
1 stop6h 32m
JetBlue
Deal found 7/2$175
This Cheapflightsfares deal was found by Cheapflights users on 7/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:07 am
BOS
-
ORD
Nonstop2h 58m
JetBlue
Wed 7/2910:56 am
ORD
-
BOS
Nonstop2h 27m
JetBlue
Deal found 7/6$177
This Delta deal was found by Cheapflights users on 7/6. 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.
Sat 7/257:59 pm
BOS
-
ORD
Nonstop3h 00m
Delta
Thu 7/303:19 pm
ORD
-
BOS
Nonstop2h 40m
Delta
Deal found 7/6$178
This Southwest deal was found by Cheapflights users on 7/2. 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.
Mon 8/246:40 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Wed 8/266:40 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 7/2$179

Find 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 July 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$170
(Southwest)

One-way from

$98
(United Airlines)

Popular in

June

Cheapest in

January

Average price

$240

Good round-trip deal

$367 or less

Good one-way deal

$225 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. 7% potential increase in price ($19 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 July 2026
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 July 6, 2026.
Use the filters below to find and compare flights from Rhode Island to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/18

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Wed 7/22

7:45 pm-11:21 pm

Nonstop2h 36m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/18

6:43 pm-8:40 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sat 7/25

6:20 pm-9:56 pm

Nonstop2h 36m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/20

5:45 am-9:38 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 8/22

6:15 am-9:36 am

Nonstop2h 21m

$172

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/4

8:15 pm-10:15 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 8/11

6:00 am-11:17 am

1 stop4h 17m

$172

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 7/29

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Sat 8/1

5:25 am-8:40 am

Nonstop2h 15m

$175

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/1

2:40 pm-9:58 pm

1 stop8h 18m

Chicago O'Hare Intl

Sat 9/5

1:49 pm-5:59 pm

Nonstop3h 10m

$175

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/22

11:05 am-12:59 pm

Nonstop2h 54m

Chicago O'Hare Intl

Mon 8/24

6:00 am-2:43 pm

1 stop7h 43m

$176

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/21

7:19 am-9:17 am

Nonstop2h 58m

Chicago O'Hare Intl

Thu 7/30

9:41 pm-1:14 am

Nonstop2h 33m

$178

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 8/31

7:30 am-9:26 am

Nonstop2h 56m

Chicago O'Hare Intl

Sat 9/12

11:30 am-3:15 pm

Nonstop2h 45m

$181

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/22

5:45 am-9:38 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 8/29

7:45 am-11:19 am

Nonstop2h 34m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 60 resultsSorted by cheapest first
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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, March is the cheapest month in which you can book a flight from Rhode Island to Chicago (average of $85). Flying from Rhode Island to Chicago in April is currently the most expensive (average of $217). 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 July 6, 2026.

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 10% versus a flight in the morning.

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 July 6, 2026.

The most flights from USRI to CHI are scheduled on a Monday (15 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

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

How far ahead should I book a flight from Rhode Island to Chicago?

The best time to book flights from Rhode Island to Chicago is 54 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 July 4, 2026.

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.

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 35m. Rhode Island and Chicago are separated by a distance of 857 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 $108. However, be on the lookout for offers from American Airlines 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 Qatar Airways (93%), Emirates (90%) or Envoy Air (89%) 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 $1,246 for a flight from Rhode Island to Chicago. The cheapest flight overall is $138 while the most popular route, (Boston Logan Intl - Chicago O'Hare Intl) is currently priced at $147.

  • 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, March is the cheapest month in which you can book a flight from Rhode Island to Chicago (average of $85). Flying from Rhode Island to Chicago in April is currently the most expensive (average of $217). 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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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 3 airlines flying from Rhode Island to Chicago

Discover the top 3 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 July 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$230Average$386FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$234Average$400FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$261Average$387FlexibilityNo cancel feeOn-time63%

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