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Cheap flights from Rhode Island to Chicago from $50

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 8/27. 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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Find the cheapest flights from Rhode Island to Chicago

Cheap round-trip flights

Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
5:55 am - 9:10 amMDW-BOS
2h 15mnonstop
$99Southwest
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Thu, Sep 4 - Sun, Sep 7
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
$105Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
12:15 pm - 1:50 pmBOS-MDW
2h 35mnonstop
Southwest Logo
11:40 am - 5:20 pmMDW-BOS
4h 40m1 stop
$109Southwest
Find Deal
Thu, Sep 11 - Sat, Sep 13
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
Southwest Logo
11:25 am - 5:20 pmMDW-BOS
4h 55m1 stop
$114Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
8:20 pm - 9:55 pmBOS-MDW
2h 35mnonstop
Southwest Logo
7:30 am - 6:10 pmMDW-BOS
9h 40m1 stop
$115Southwest
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Fri, Sep 12 - Mon, Sep 15
Frontier Logo
9:28 am - 7:11 amBOS-MDW
22h 43m1 stop
Frontier Logo
6:15 am - 9:58 amMDW-BOS
26h 43m1 stop
$161Frontier
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Thu, Sep 4 - Sat, Sep 6
Frontier Logo
10:10 am - 6:18 pmBOS-MDW
9h 08m1 stop
Frontier Logo
7:23 pm - 9:15 amMDW-BOS
12h 52m1 stop
$172Frontier
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Fri, Oct 31 - Sun, Nov 2
Allegiant Air Logo
8:59 am - 4:43 pmBOS-MDW
8h 44m1 stop
Allegiant Air Logo
7:50 pm - 9:43 amMDW-BOS
12h 53m1 stop
$215Allegiant Air
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Fri, Sep 5 - Mon, Sep 8
Delta Logo
12:55 pm - 6:25 pmPVD-MDW
6h 30m1 stop
Delta Logo
6:00 am - 12:07 pmMDW-PVD
5h 07m1 stop
$217Delta
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Wed, Oct 8 - Wed, Dec 3
Delta Logo
2:12 pm - 9:10 pmPVD-MDW
7h 58m1 stop
Delta Logo
6:00 am - 12:07 pmMDW-PVD
5h 07m1 stop
$237Delta
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Sat, Oct 4 - Mon, Dec 8

Southwest flights from Rhode Island to Chicago Midway Airport

Our best Southwest deals on Rhode Island to Chicago Midway Airport flight tickets
Southwest
Sep 4
BOS5:15 amBoston Logan Intl
2h 30m
MDW6:45 amChicago Midway
Sep 7
MDW5:55 amChicago Midway
2h 15m
BOS9:10 amBoston Logan Intl
$99
Find similar
Southwest
Dec 4
BOS5:35 pmBoston Logan Intl
4h 30m
1 stop
MDW9:05 pmChicago Midway
Dec 8
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
$105
Find similar
Southwest
Sep 11
BOS12:15 pmBoston Logan Intl
2h 35m
MDW1:50 pmChicago Midway
Sep 13
MDW11:40 amChicago Midway
4h 40m
1 stop
BOS5:20 pmBoston Logan Intl
$109
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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
Sep 4
BOS9:28 amBoston Logan Intl
22h 43m
1 stop
MDW7:11 amChicago Midway
Sep 6
MDW6:15 amChicago Midway
26h 43m
1 stop
BOS9:58 amBoston Logan Intl
$161
Find similar
Frontier
Oct 31
BOS10:10 amBoston Logan Intl
9h 08m
1 stop
MDW6:18 pmChicago Midway
Nov 2
MDW7:23 pmChicago Midway
12h 52m
1 stop
BOS9:15 amBoston Logan Intl
$172
Find similar
Frontier
Sep 4
BOS10:53 amBoston Logan Intl
6h 05m
1 stop
MDW3:58 pmChicago Midway
Sep 6
MDW11:23 amChicago Midway
21h 35m
2 stops
BOS9:58 amBoston Logan Intl
$190
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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 August 14, 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

Thu 9/4

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Sun 9/7

5:55 am-9:10 am

Nonstop2h 15m

$99

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/4

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Mon 12/8

6:15 pm-9:35 pm

Nonstop2h 20m

$105

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/11

12:15 pm-1:50 pm

Nonstop2h 35m

Chicago Midway

Sat 9/13

11:40 am-5:20 pm

1 stop4h 40m

$109

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/4

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Mon 12/8

11:25 am-5:20 pm

1 stop4h 55m

$114

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/12

8:20 pm-9:55 pm

Nonstop2h 35m

Chicago Midway

Mon 9/15

7:30 am-6:10 pm

1 stop9h 40m

$115

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

9:28 am-7:11 am

1 stop22h 43m

Chicago Midway

Sat 9/6

6:15 am-9:58 am

1 stop26h 43m

$161

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/31

10:10 am-6:18 pm

1 stop9h 08m

Chicago Midway

Sun 11/2

7:23 pm-9:15 am

1 stop12h 52m

$172

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/5

8:59 am-4:43 pm

1 stop8h 44m

Chicago Midway

Mon 9/8

7:50 pm-9:43 am

1 stop12h 53m

$215

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Wed 10/8

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Wed 12/3

6:00 am-12:07 pm

1 stop5h 07m

$217

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Sat 10/4

2:12 pm-9:10 pm

1 stop7h 58m

Chicago Midway

Mon 12/8

6:00 am-12:07 pm

1 stop5h 07m

$237

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 $206.

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 $294. 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 $431.

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

Flying to Chicago Midway Airport from Rhode Island at noon is the least expensive time of day to depart. momondo users have found prices as low as $321 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $343. 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 $252 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 $170 on momondo.

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

There are 1 cabin classes 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?

No. A direct flight is the cheapest option for a flight between Rhode Island to Chicago Midway Airport.

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

$50

Fastest flight time

2h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Rhode Island in the past 72 hours is $50. The best round-trip flight deal from Rhode Island to Chicago Midway Airport found on momondo in the last 72 hours is $99.
The fastest flight from Rhode Island to Chicago Midway Airport takes 2h 25m
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 $204Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
American AirlinesPriceFrom $232Free CancellationRating
7.2
10,000 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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