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$85+ Cheap flights from Grand Rapids (GRR) to Midway (MDW)

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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — MDW
Apr 26 — May 31
Sun 4/26
Sun 5/3
1 adult, Economy
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Cheap flight deals from Grand Rapids to Midway

Cheapest flights from Grand Rapids to Midway
Explore the most affordable flight options available from Grand Rapids to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 27, 2026.

This Southwest deal was found by Cheapflights users on 3/24. 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 4/215:05 pm
GRR
-
MDW
Nonstop1h 05m
Southwest
Tue 4/289:40 pm
MDW
-
GRR
Nonstop0h 55m
Southwest
Deal found 3/24$169
This Southwest deal was found by Cheapflights users on 3/22. 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.
Wed 4/225:05 pm
GRR
-
MDW
Nonstop1h 05m
Southwest
Wed 4/229:40 pm
MDW
-
GRR
Nonstop0h 55m
Southwest
Deal found 3/22$170
This Southwest deal was found by Cheapflights users on 3/25. 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 4/275:40 pm
GRR
-
MDW
Nonstop1h 05m
Southwest
Wed 4/2910:15 am
MDW
-
GRR
Nonstop0h 55m
Southwest
Deal found 3/25$186
This Southwest deal was found by Cheapflights users on 3/26. 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 4/256:45 am
GRR
-
MDW
Nonstop1h 00m
Southwest
Sat 4/2510:10 am
MDW
-
GRR
Nonstop0h 55m
Southwest
Deal found 3/26$191
This Southwest deal was found by Cheapflights users on 3/26. 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 4/253:05 pm
GRR
-
MDW
1 stop6h 35m
Southwest
Sat 5/26:10 am
MDW
-
GRR
1 stop7h 20m
Southwest
Deal found 3/26$211
This Southwest deal was found by Cheapflights users on 3/26. 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 5/86:30 am
GRR
-
MDW
Nonstop1h 05m
Southwest
Tue 5/1210:15 am
MDW
-
GRR
Nonstop0h 55m
Southwest
Deal found 3/26$212
This Delta deal was found by Cheapflights users on 3/26. 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 4/183:50 pm
GRR
-
MDW
1 stop3h 08m
Delta
Mon 4/206:38 pm
MDW
-
GRR
1 stop4h 19m
Delta
Deal found 3/26$223

Find flight deals from Grand Rapids to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Grand Rapids (GRR) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$169
(Southwest)

One-way from

$85
(Southwest)

Popular in

January

Cheapest in

October

Average price

$217

Good round-trip deal

$393 or less

Good one-way deal

$198 or less
Provider with most accurate pricing for Grand Rapids Gerald R. Ford Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Grand Rapids Gerald R. Ford Intl-Chicago Midway flights.
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From Grand Rapids Gerald R. Ford Intl to Chicago Midway
Search Deals
One-way flight from Grand Rapids Gerald R. Ford Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 31% potential increase in price ($133 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Grand Rapids Gerald R. Ford Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Grand Rapids Gerald R. Ford Intl to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Grand Rapids to Midway 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 March 27, 2026.
Use the filters below to find and compare flights from Grand Rapids to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Mon 4/27

8:25 am-1:10 pm

2 stops5h 45m

Chicago Midway

Wed 4/29

10:15 am-12:10 pm

Nonstop0h 55m

$201
Quickest round-trip

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 4/25

6:45 am-6:45 am

Nonstop1h 00m

Chicago Midway

Sat 4/25

9:05 am-2:30 pm

1 stop4h 25m

$201

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 4/21

8:10 am-3:50 pm

2 stops8h 40m

Chicago Midway

Tue 4/28

5:00 pm-10:35 pm

1 stop4h 35m

$245

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sun 5/31

2:21 pm-6:33 pm

1 stop5h 12m

Chicago Midway

Mon 6/1

9:22 am-1:40 pm

1 stop3h 18m

$273

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 9/19

6:30 am-6:40 am

Nonstop1h 10m

Chicago Midway

Sat 9/26

5:55 am-11:20 am

1 stop4h 25m

$273

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sun 4/19

5:30 am-1:05 pm

2 stops8h 35m

Chicago Midway

Wed 4/22

10:15 am-12:10 pm

Nonstop0h 55m

$279

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 6/11

6:00 pm-6:05 pm

Nonstop1h 05m

Chicago Midway

Sun 6/14

6:10 am-1:25 pm

1 stop6h 15m

$292
Cheapest one-way

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 5/27

5:30 am-1:19 pm

2 stops8h 49m

$100

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 4/28

5:29 am-1:32 pm

2 stops9h 03m

$100

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 4/25

10:31 am-12:43 pm

1 stop3h 12m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Compare providers for flights from Grand Rapids to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Grand Rapids to Midway in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Grand Rapids-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Grand Rapids-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Grand Rapids-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Grand Rapids-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Grand Rapids-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Grand Rapids to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Grand Rapids 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 Grand Rapids to Chicago Midway Airport

What is the cheapest time of day to fly from GRR to MDW?

Find hourly flight availability from Grand Rapids to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 27, 2026.

It’s optimal to fly from Grand Rapids to Chicago Midway Airport in the evening. By choosing this option you can save up to 10% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Grand Rapids to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Grand Rapids to Midway. Price data was last updated on March 23, 2026.

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

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated March 27, 2026.
See what other customers who have flown with Southwest from Grand Rapids to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Grand Rapids to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Grand Rapids to Chicago Midway?

    If you book a flight to Chicago Midway from Grand Rapids, you will be flying from Gerald R. Ford Intl, which is the city’s only airport. Grand Rapids Gerald R. Ford Intl (GRR) is located 9.2 mi from the center of Grand Rapids. There are 2 flights from Gerald R. Ford Intl to Chicago Midway per day from 1 airline.

  • How long is the flight from Grand Rapids to Chicago Midway Airport?

    Southwest can get you from Grand Rapids to Chicago Midway Airport in just under 5h 45m. Your travel time can differ by up to . The distance from Grand Rapids to Chicago Midway Airport is about 136 mi.

  • What is the cheapest airline to fly from Grand Rapids to Chicago Midway Airport round-trip?

    Our cheapest airline available from Grand Rapids to Chicago Midway Airport is Southwest. Our recent data shows that you can find tickets from as low as $97 on this airline.

  • What are the cheapest flights from Grand Rapids to Chicago Midway Airport?

    The cheapest flight price from Grand Rapids to Chicago Midway Airport is $139. On average you can expect to pay $352. The most popular route, (Grand Rapids Gerald R. Ford Intl - Chicago Midway), can usually be booked for $191.

  • Can I find deals for flights from Grand Rapids to Midway that include hotel bookings?

    Yes. In addition to deals on Grand Rapids to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Grand Rapids to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Grand Rapids to Midway.

  • Can I find deals for business class flights from Grand Rapids to Midway?

    Yes. Cheapflights offers flight deals from Grand Rapids to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Grand Rapids to Midway

Discover the top airline that operate flights from Grand Rapids to Midway. 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 March 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$201FlexibilityNo cancel feeOn-time63%

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