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Cheap flights from Rhode Island to Chicago from $64

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 3/25. 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

Enter your travel dates to find the best prices.
Southwest Logo
3:30 pm - 5:15 pm
BOS
-
MDW
2h 45mnonstop
Southwest Logo
6:05 pm - 9:25 pm
MDW
-
BOS
2h 20mnonstop
$129Southwest
Sat, May 2 - Sat, May 9
Southwest Logo
2:00 pm - 3:45 pm
BOS
-
MDW
2h 45mnonstop
Southwest Logo
3:15 pm - 6:35 pm
MDW
-
BOS
2h 20mnonstop
$130Southwest
Wed, Mar 11 - Wed, Apr 29
Southwest Logo
7:10 am - 9:00 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
7:00 pm - 10:20 pm
MDW
-
BOS
2h 20mnonstop
$132Southwest
Thu, May 7 - Mon, May 11
Southwest Logo
7:15 am - 9:05 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
12:45 pm - 4:05 pm
MDW
-
BOS
2h 20mnonstop
$133Southwest
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
7:15 am - 9:10 am
BOS
-
MDW
2h 55mnonstop
Southwest Logo
4:35 pm - 11:55 pm
MDW
-
BOS
6h 20m
1 stop
$135Southwest
Tue, Mar 31 - Sat, Apr 4
Southwest Logo
6:00 pm - 7:50 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
2:35 pm - 5:45 pm
MDW
-
BOS
2h 10mnonstop
$137Southwest
Tue, Mar 24 - Tue, Mar 31
Southwest Logo
7:15 am - 9:10 am
BOS
-
MDW
2h 55mnonstop
Southwest Logo
6:45 pm - 10:00 pm
MDW
-
BOS
2h 15mnonstop
$138Southwest
Wed, Mar 25 - Sat, Mar 28
Southwest Logo
2:25 pm - 4:05 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
$141Southwest
Tue, Apr 14 - Mon, Apr 20
Southwest Logo
2:25 pm - 4:05 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
3:00 pm - 10:30 pm
MDW
-
BOS
6h 30m
1 stop
$142Southwest
Tue, Apr 7 - Tue, Apr 21
Southwest Logo
7:15 am - 9:10 am
BOS
-
MDW
2h 55mnonstop
Southwest Logo
6:10 pm - 9:25 pm
MDW
-
BOS
2h 15mnonstop
$145Southwest
Mon, Mar 9 - Wed, Mar 11

Delta flights from Rhode Island to Chicago Midway Airport

Our best Delta deals on Rhode Island to Chicago Midway Airport flight tickets
Delta
Apr 14
BOS5:30 amBoston Logan Intl
4h 17m
1 stop
MDW8:47 amChicago Midway
Apr 15
MDW9:27 amChicago Midway
6h 03m
1 stop
BOS4:30 pmBoston Logan Intl
$184
Delta
Mar 18
PVD5:29 amProvidence-TFGreen
4h 24m
1 stop
MDW8:53 amChicago Midway
Mar 21
MDW6:34 pmChicago Midway
3h 45m
1 stop
PVD11:19 pmProvidence-TFGreen
$329
Delta
Mar 18
PVD5:29 amProvidence-TFGreen
4h 24m
1 stop
MDW8:53 amChicago Midway
Mar 21
MDW6:34 pmChicago Midway
3h 45m
1 stop
PVD11:19 pmProvidence-TFGreen
$331

Southwest flights from Rhode Island to Chicago Midway Airport

Our best Southwest deals on Rhode Island to Chicago Midway Airport flight tickets
Southwest
May 2
BOS3:30 pmBoston Logan Intl
2h 45m
MDW5:15 pmChicago Midway
May 9
MDW6:05 pmChicago Midway
2h 20m
BOS9:25 pmBoston Logan Intl
$129
Southwest
Mar 11
BOS2:00 pmBoston Logan Intl
2h 45m
MDW3:45 pmChicago Midway
Apr 29
MDW3:15 pmChicago Midway
2h 20m
BOS6:35 pmBoston Logan Intl
$130
Southwest
Mar 30
BOS3:10 pmBoston Logan Intl
2h 45m
MDW4:55 pmChicago Midway
Apr 13
MDW7:00 pmChicago Midway
2h 20m
BOS10:20 pmBoston Logan Intl
$132

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 February 25, 2026.
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

Sat 5/2

3:30 pm-5:15 pm

Nonstop2h 45m

Chicago Midway

Sat 5/9

6:05 pm-9:25 pm

Nonstop2h 20m

$129

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 3/11

2:00 pm-3:45 pm

Nonstop2h 45m

Chicago Midway

Wed 4/29

3:15 pm-6:35 pm

Nonstop2h 20m

$130

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 5/7

7:10 am-9:00 am

Nonstop2h 50m

Chicago Midway

Mon 5/11

7:00 pm-10:20 pm

Nonstop2h 20m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 4/11

7:15 am-9:05 am

Nonstop2h 50m

Chicago Midway

Tue 4/14

12:45 pm-4:05 pm

Nonstop2h 20m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 3/31

7:15 am-9:10 am

Nonstop2h 55m

Chicago Midway

Sat 4/4

4:35 pm-11:55 pm

1 stop6h 20m

$135

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 3/24

6:00 pm-7:50 pm

Nonstop2h 50m

Chicago Midway

Tue 3/31

2:35 pm-5:45 pm

Nonstop2h 10m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 3/25

7:15 am-9:10 am

Nonstop2h 55m

Chicago Midway

Sat 3/28

6:45 pm-10:00 pm

Nonstop2h 15m

$138

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 4/14

2:25 pm-4:05 pm

Nonstop2h 40m

Chicago Midway

Mon 4/20

7:40 am-10:55 am

Nonstop2h 15m

$141

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 4/7

2:25 pm-4:05 pm

Nonstop2h 40m

Chicago Midway

Tue 4/21

3:00 pm-10:30 pm

1 stop6h 30m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 3/9

7:15 am-9:10 am

Nonstop2h 55m

Chicago Midway

Wed 3/11

6:10 pm-9:25 pm

Nonstop2h 15m

$145

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from Rhode Island, with most prices found around $137. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Rhode Island during the month January is also very affordable. Most momondo users find prices during this month for around $162.

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 $285. 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 $400.

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 $248 when looking at flights departing in the evening. 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 $257 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 $135 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?

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

$193

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 $193. The best round-trip flight deal from Rhode Island to Chicago Midway Airport found on momondo in the last 72 hours is $366.
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 $261Free CancellationRating
8.0
4,299 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Porter
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Saint John

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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