$49 Cheap Flights from Grand Rapids (GRR) to Chicago (MDW)

View $49 flight on Tue, Dec 16, 2025Opens in a new window

Popular airlines from Gerald R. Ford International Airport (GRR) to Chicago Midway Airport (MDW)

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Cheap Flights from Grand Rapids to Chicago (GRR-MDW)

Prices were available within the past 7 days and start at $49 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Dec 16 - Wed, Dec 17
GRR
Grand Rapids
MDW
Chicago
$97 Roundtrip, found 3 hours ago
$97
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Grand Rapids to Chicago, returning Wed, Dec 17, priced at $97 found 3 hours ago
Southwest Airlines
Tue, Dec 16 - Wed, Dec 17
GRR
Grand Rapids
MDW
Chicago
$107 Roundtrip, found 3 hours ago
$107
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Grand Rapids to Chicago, returning Wed, Dec 17, priced at $107 found 3 hours ago
Southwest Airlines
Tue, Dec 16 - Wed, Dec 17
GRR
Grand Rapids
MDW
Chicago
$117 Roundtrip, found 3 hours ago
$117
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Grand Rapids to Chicago, returning Wed, Dec 17, priced at $117 found 3 hours ago
Southwest Airlines
Thu, Nov 27 - Wed, Dec 3
GRR
Grand Rapids
MDW
Chicago
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Nov 27 from Grand Rapids to Chicago, returning Wed, Dec 3, priced at $124 found 2 days ago
Southwest Airlines
Thu, Nov 27 - Wed, Dec 3
GRR
Grand Rapids
MDW
Chicago
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Nov 27 from Grand Rapids to Chicago, returning Wed, Dec 3, priced at $134 found 2 days ago
Southwest Airlines
Sat, Dec 13 - Mon, Dec 15
GRR
Grand Rapids
MDW
Chicago
$155 Roundtrip, found 4 days ago
$155
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Grand Rapids to Chicago, returning Mon, Dec 15, priced at $155 found 4 days ago
Delta
Wed, Dec 3 - Thu, Dec 4
GRR
Grand Rapids
MDW
Chicago
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Delta flight, departing Wed, Dec 3 from Grand Rapids to Chicago, returning Thu, Dec 4, priced at $157 just found
Southwest Airlines
Tue, Dec 16 - Wed, Dec 17
GRR
Grand Rapids
MDW
Chicago
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Grand Rapids to Chicago, returning Wed, Dec 17, priced at $157 found 3 hours ago
Delta
Thu, Nov 27 - Wed, Dec 3
GRR
Grand Rapids
MDW
Chicago
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 27 from Grand Rapids to Chicago, returning Wed, Dec 3, priced at $162 found 2 days ago
Southwest Airlines
Wed, Nov 26 - Wed, Dec 3
GRR
Grand Rapids
MDW
Chicago
$166 Roundtrip, found 3 hours ago
$166
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Nov 26 from Grand Rapids to Chicago, returning Wed, Dec 3, priced at $166 found 3 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $403
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $403

Frequently asked questions

How much does a flight from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $49 or cheap return flight from $97 from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
The cheapest month to fly from GRR to MDW is December, when there's less demand. Off-peak months are typically when you'll find lower airfares between these airports.
Which airlines fly direct from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
Take a nonstop flight with Southwest Airlines and travel straight from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll take you from GRR to MDW. Then, sort your results by "Price (lowest to highest)" to pick up a great deal.
How many flights per day from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
When flying out of Gerald R. Ford Intl. Airport (GRR), you'll have a choice from an average of 2 daily nonstop flights to Midway Intl. Airport (MDW).
What are the most popular departure times for flights from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
More people fly between GRR and MDW at 7 AM than at any other time of day. Looking for a quieter experience? Consider flying outside peak hours and there's a chance you'll save on your fare as well.
What day of the week has the most flights from GRR to MDW?
Friday offers the most flights from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW). Consider leaving on this day and you'll have the best chance of finding a schedule that works for you.
What is the earliest flight from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
Gerald R. Ford Intl. Airport (GRR)'s earliest flight to Midway Intl. Airport (MDW) is at approximately 7:10AM UTC-5. With a travel duration of 1h 15m, you'll land at around 7:25AM UTC-6.
How long does it take to fly from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
It takes roughly 1 hour and 10 minutes to travel the 140 mi from GRR to MDW.
What airline has the least delays from GRR to MDW?
With 85% of flights usually landing on schedule, Southwest Airlines has the best on-time performance for direct flights from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW). To keep track of your flight status and get notified if anything changes, simply head to the Expedia App.
What is the best time to fly from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
Book a flight from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the risk of cancellations. Later departures are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Gerald R. Ford Intl. Airport (GRR)?
If you're departing on a direct flight from Gerald R. Ford Intl. Airport (GRR) to Chicago, you'll land at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW) last-minute?
Waiting until right before your break to book a ticket from GRR to MDW often results in higher prices. While you may find some last-minute deals, they're not always guaranteed. Keep your travel schedule open to maximize your chances of snagging a bargain.
Is it cheaper to book a GRR to MDW flight and hotel package?
Securing a GRR to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Choose from our extensive range of hotels and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Gerald R. Ford Intl. Airport (GRR) to Midway Intl. Airport (MDW)?
If you reserved your GRR to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

0
Origin airport
Gerald R. Ford Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$97
Distance
135 mi

Book with confidence

Grand Rapids to Chicago Flights

The cheapest times to fly from Grand Rapids to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Grand Rapids to Chicago are during the month of December. You can find some of the cheapest flights from Grand Rapids to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Grand Rapids to Chicago

Sunday is one of the best days to book for cheap flights from Grand Rapids to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Grand Rapids to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Grand Rapids to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $49 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Grand Rapids to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Grand Rapids to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Grand Rapids to Chicago Flights

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