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Cheap flights from Rhode Island to Chicago from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Rhode Island to Chicago departing on 10/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

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Southwest Logo
2:40 pm - 8:35 pmBOS-MDW
6h 55m1 stop
Southwest Logo
9:20 pm - 12:40 amMDW-BOS
2h 20mnonstop
$127Southwest
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Mon, Oct 20 - Thu, Oct 23
Southwest Logo
11:55 am - 7:10 pmBOS-MDW
8h 15m2 stops
Southwest Logo
6:30 am - 9:45 amMDW-BOS
2h 15mnonstop
$132Southwest
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Wed, Oct 22 - Sat, Oct 25
Southwest Logo
5:00 am - 9:05 amBOS-MDW
5h 05m1 stop
Southwest Logo
11:25 am - 5:20 pmMDW-BOS
4h 55m1 stop
$137Southwest
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Thu, Oct 30 - Mon, Nov 3
Southwest Logo
12:00 pm - 7:35 pmBOS-MDW
8h 35m2 stops
Southwest Logo
4:55 pm - 10:55 pmMDW-BOS
5h 00m1 stop
$142Southwest
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Fri, Jan 16 - Mon, Jan 19
Frontier Logo
9:39 am - 2:33 pmBOS-MDW
5h 54m1 stop
Frontier Logo
5:20 am - 8:00 amMDW-BOS
25h 40m1 stop
$159Frontier
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Thu, Oct 30 - Sun, Nov 2
Frontier Logo
9:39 am - 2:33 pmBOS-MDW
5h 54m1 stop
Frontier Logo
5:20 am - 8:00 amMDW-BOS
25h 40m1 stop
$160Frontier
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Thu, Oct 30 - Sun, Nov 2
Multiple Airlines Logo
12:00 pm - 11:55 pmBOS-MDW
12h 55m2 stops
Multiple Airlines Logo
2:06 pm - 9:00 amMDW-BOS
17h 54m1 stop
$174Multiple Airlines
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Tue, Nov 4 - Wed, Nov 5
Multiple Airlines Logo
9:39 am - 2:33 pmBOS-MDW
5h 54m1 stop
Multiple Airlines Logo
6:20 am - 12:26 amMDW-BOS
17h 06m1 stop
$175Multiple Airlines
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Thu, Oct 30 - Sat, Nov 1
Delta Logo
12:55 pm - 5:55 pmPVD-MDW
6h 00m1 stop
Delta Logo
4:23 pm - 11:58 pmMDW-PVD
6h 35m1 stop
$275Delta
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Fri, Oct 31 - Sat, Nov 8
Delta Logo
12:55 pm - 5:55 pmPVD-MDW
6h 00m1 stop
Delta Logo
9:35 am - 4:23 pmMDW-PVD
5h 48m1 stop
$282Delta
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Fri, Oct 31 - Mon, Nov 3

Southwest flights from Rhode Island to Chicago Midway Airport

Our best Southwest deals on Rhode Island to Chicago Midway Airport flight tickets
Southwest
Oct 20
BOS2:40 pmBoston Logan Intl
6h 55m
1 stop
MDW8:35 pmChicago Midway
Oct 23
MDW9:20 pmChicago Midway
2h 20m
BOS12:40 amBoston Logan Intl
$127
Find similar
Southwest
Oct 22
BOS11:55 amBoston Logan Intl
8h 15m
2 stops
MDW7:10 pmChicago Midway
Oct 25
MDW6:30 amChicago Midway
2h 15m
BOS9:45 amBoston Logan Intl
$132
Find similar
Southwest
Oct 30
BOS5:00 amBoston Logan Intl
5h 05m
1 stop
MDW9:05 amChicago Midway
Nov 3
MDW11:25 amChicago Midway
4h 55m
1 stop
BOS5:20 pmBoston Logan Intl
$137
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Frontier flights from Rhode Island to Chicago Midway Airport

Our best Frontier deals on Rhode Island to Chicago Midway Airport flight tickets
Frontier
Oct 30
BOS9:39 amBoston Logan Intl
5h 54m
1 stop
MDW2:33 pmChicago Midway
Nov 2
MDW5:20 amChicago Midway
25h 40m
1 stop
BOS8:00 amBoston Logan Intl
$159
Find similar
Frontier
Oct 30
BOS9:39 amBoston Logan Intl
5h 54m
1 stop
MDW2:33 pmChicago Midway
Nov 2
MDW5:20 amChicago Midway
25h 40m
1 stop
BOS8:00 amBoston Logan Intl
$160
Find similar
Frontier
Dec 9
BOS6:00 amBoston Logan Intl
16h 32m
1 stop
MDW9:32 pmChicago Midway
Dec 14
MDW6:00 amChicago Midway
17h 44m
1 stop
BOS12:44 amBoston Logan Intl
$171
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momondo Fare Finder

 
Customize your flight search to find flights from Rhode Island to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated October 6, 2025.
Use the filters below to find and compare flights from Rhode Island to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 10/20

2:40 pm-8:35 pm

1 stop6h 55m

Chicago Midway

Thu 10/23

9:20 pm-12:40 am

Nonstop2h 20m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/22

11:55 am-7:10 pm

2 stops8h 15m

Chicago Midway

Sat 10/25

6:30 am-9:45 am

Nonstop2h 15m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/30

5:00 am-9:05 am

1 stop5h 05m

Chicago Midway

Mon 11/3

11:25 am-5:20 pm

1 stop4h 55m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/16

12:00 pm-7:35 pm

2 stops8h 35m

Chicago Midway

Mon 1/19

4:55 pm-10:55 pm

1 stop5h 00m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/30

9:39 am-2:33 pm

1 stop5h 54m

Chicago Midway

Sun 11/2

5:20 am-8:00 am

1 stop25h 40m

$159

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/30

9:39 am-2:33 pm

1 stop5h 54m

Chicago Midway

Sun 11/2

5:20 am-8:00 am

1 stop25h 40m

$160

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 11/4

12:00 pm-11:55 pm

2 stops12h 55m

Chicago Midway

Wed 11/5

2:06 pm-9:00 am

1 stop17h 54m

$174

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/30

9:39 am-2:33 pm

1 stop5h 54m

Chicago Midway

Sat 11/1

6:20 am-12:26 am

1 stop17h 06m

$175

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Fri 10/31

12:55 pm-5:55 pm

1 stop6h 00m

Chicago Midway

Sat 11/8

4:23 pm-11:58 pm

1 stop6h 35m

$275

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Fri 10/31

12:55 pm-5:55 pm

1 stop6h 00m

Chicago Midway

Mon 11/3

9:35 am-4:23 pm

1 stop5h 48m

$282

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Rhode Island to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Rhode Island, with most prices found around $200. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Rhode Island during the month September is also very affordable. Most momondo users find prices during this month for around $213.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Rhode Island. The lowest ticket price found for a Wednesday departure recently was $297. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Rhode Island because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $426.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Rhode Island in the evening is the least expensive time of day to depart. momondo users have found prices as low as $310 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $348. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Rhode Island to Chicago Midway flight route?

Fly from Providence-TFGreen to Chicago Midway for the best Rhode Island - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Rhode Island when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $266 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Rhode Island for as low as $164 on momondo.

What cabin class options are available on Rhode Island to Chicago Midway flights?

There is only 1 cabin class available to choose from on Rhode Island to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Rhode Island to Chicago Midway Airport flights?

You could potentially save up to 12% on your flight if you consider stops on a Rhode Island to Chicago Midway Airport flight.

Cheap Rhode Island to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Rhode Island to Chicago Midway Airport

Best Price Found

$189

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Rhode Island in the past 72 hours is $189. The best round-trip flight deal from Rhode Island to Chicago Midway Airport found on momondo in the last 72 hours is $343.
The fastest flight from Rhode Island to Chicago Midway Airport takes 2h 30m
Direct flights go from Rhode Island to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Rhode Island to Chicago Midway Airport?

    Prices for flights from Rhode Island to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Rhode Island to Chicago Midway Airport?

  • How old do you have to be to fly from Rhode Island to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Rhode Island to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Rhode Island to Chicago Midway Airport?

Best airlines flying from Rhode Island to Chicago Midway Airport

Compare and see reviews for airlines that fly from Rhode Island to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $207Free CancellationRating
8.0
4,232 reviews
Search Southwest flights
American AirlinesPriceFrom $232Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Why use momondo?

Why should I use momondo to find a flight deal from Rhode Island to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Rhode Island.

Can I find flights from Rhode Island to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Rhode Island on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Rhode Island to Chicago?

Once all potential Rhode Island to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Rhode Island to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Rhode Island and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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