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Cheap flights from Grand Rapids to Chicago from $32

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Grand Rapids to Chicago departing on 1/20. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:23 am - 8:52 am
GRR
-
MDW
4h 29m1 stop
Delta Logo
9:32 am - 1:32 pm
MDW
-
GRR
3h 00m1 stop
$157Delta
Thu, Jan 8 - Mon, Jan 12
Delta Logo
7:05 am - 1:09 pm
GRR
-
MDW
7h 04m1 stop
Delta Logo
9:32 am - 5:56 pm
MDW
-
GRR
7h 24m2 stops
$162Delta
Tue, Jan 20 - Wed, Jan 21
Southwest Logo
4:20 pm - 4:40 pm
GRR
-
MDW
1h 20mnonstop
Southwest Logo
8:05 pm - 10:00 pm
MDW
-
GRR
0h 55mnonstop
$163Southwest
Tue, Jan 6 - Tue, Jan 6
Delta Logo
7:05 am - 12:51 pm
GRR
-
MDW
6h 46m2 stops
Delta Logo
9:32 am - 5:56 pm
MDW
-
GRR
7h 24m2 stops
$167Delta
Tue, Jan 20 - Wed, Jan 21
Southwest Logo
5:00 pm - 5:10 pm
GRR
-
MDW
1h 10mnonstop
Southwest Logo
1:50 pm - 3:45 pm
MDW
-
GRR
0h 55mnonstop
$203Southwest
Tue, Feb 17 - Wed, Mar 4
Delta Logo
8:20 am - 12:46 pm
GRR
-
MDW
5h 26m1 stop
Delta Logo
9:33 am - 3:17 pm
MDW
-
GRR
4h 44m1 stop
$206Delta
Sat, Jan 24 - Fri, Feb 6
Southwest Logo
5:00 pm - 5:10 pm
GRR
-
MDW
1h 10mnonstop
Southwest Logo
9:45 am - 11:40 am
MDW
-
GRR
0h 55mnonstop
$207Southwest
Thu, Feb 5 - Sat, Feb 7
Southwest Logo
5:00 pm - 5:10 pm
GRR
-
MDW
1h 10mnonstop
Southwest Logo
6:50 am - 2:20 pm
MDW
-
GRR
6h 30m1 stop
$213Southwest
Tue, Feb 17 - Wed, Mar 4
Southwest Logo
6:55 am - 7:05 am
GRR
-
MDW
1h 10mnonstop
Southwest Logo
8:05 pm - 10:00 pm
MDW
-
GRR
0h 55mnonstop
$216Southwest
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
5:00 pm - 5:10 pm
GRR
-
MDW
1h 10mnonstop
Southwest Logo
6:40 am - 12:40 pm
MDW
-
GRR
5h 00m1 stop
$217Southwest
Thu, Feb 5 - Sat, Feb 7

Southwest flights from Grand Rapids to Chicago Midway Airport

Our best Southwest deals on Grand Rapids to Chicago Midway Airport flight tickets
Southwest
Feb 5
GRR5:00 pmGrand Rapids Gerald R. Ford Intl
1h 10m
MDW5:10 pmChicago Midway
Feb 7
MDW9:45 amChicago Midway
0h 55m
GRR11:40 amGrand Rapids Gerald R. Ford Intl
$207
Find similar
Southwest
Jan 8
GRR6:55 amGrand Rapids Gerald R. Ford Intl
1h 10m
MDW7:05 amChicago Midway
Jan 12
MDW8:05 pmChicago Midway
0h 55m
GRR10:00 pmGrand Rapids Gerald R. Ford Intl
$216
Find similar
Southwest
Feb 5
GRR5:00 pmGrand Rapids Gerald R. Ford Intl
1h 10m
MDW5:10 pmChicago Midway
Feb 7
MDW6:40 amChicago Midway
5h 00m
1 stop
GRR12:40 pmGrand Rapids Gerald R. Ford Intl
$217
Find similar

Delta flights from Grand Rapids to Chicago Midway Airport

Our best Delta deals on Grand Rapids to Chicago Midway Airport flight tickets
Delta
Jan 8
GRR5:23 amGrand Rapids Gerald R. Ford Intl
4h 29m
1 stop
MDW8:52 amChicago Midway
Jan 12
MDW9:32 amChicago Midway
3h 00m
1 stop
GRR1:32 pmGrand Rapids Gerald R. Ford Intl
$157
Find similar
Delta
Jan 20
GRR7:05 amGrand Rapids Gerald R. Ford Intl
7h 04m
1 stop
MDW1:09 pmChicago Midway
Jan 21
MDW9:32 amChicago Midway
7h 24m
2 stops
GRR5:56 pmGrand Rapids Gerald R. Ford Intl
$162
Find similar
Delta
Jan 20
GRR7:05 amGrand Rapids Gerald R. Ford Intl
6h 46m
2 stops
MDW12:51 pmChicago Midway
Jan 21
MDW9:32 amChicago Midway
7h 24m
2 stops
GRR5:56 pmGrand Rapids Gerald R. Ford Intl
$167
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Grand Rapids 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 December 4, 2025.
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

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 1/8

5:23 am-8:52 am

1 stop4h 29m

Chicago Midway

Mon 1/12

9:32 am-1:32 pm

1 stop3h 00m

$157

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 1/20

7:05 am-1:09 pm

1 stop7h 04m

Chicago Midway

Wed 1/21

9:32 am-5:56 pm

2 stops7h 24m

$162

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 1/6

4:20 pm-4:40 pm

Nonstop1h 20m

Chicago Midway

Tue 1/6

8:05 pm-10:00 pm

Nonstop0h 55m

$163

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 1/20

7:05 am-12:51 pm

2 stops6h 46m

Chicago Midway

Wed 1/21

9:32 am-5:56 pm

2 stops7h 24m

$167

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 2/17

5:00 pm-5:10 pm

Nonstop1h 10m

Chicago Midway

Wed 3/4

1:50 pm-3:45 pm

Nonstop0h 55m

$203

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 1/24

8:20 am-12:46 pm

1 stop5h 26m

Chicago Midway

Fri 2/6

9:33 am-3:17 pm

1 stop4h 44m

$206

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 2/5

5:00 pm-5:10 pm

Nonstop1h 10m

Chicago Midway

Sat 2/7

9:45 am-11:40 am

Nonstop0h 55m

$207

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 2/17

5:00 pm-5:10 pm

Nonstop1h 10m

Chicago Midway

Wed 3/4

6:50 am-2:20 pm

1 stop6h 30m

$213

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 1/8

6:55 am-7:05 am

Nonstop1h 10m

Chicago Midway

Mon 1/12

8:05 pm-10:00 pm

Nonstop0h 55m

$216

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 2/5

5:00 pm-5:10 pm

Nonstop1h 10m

Chicago Midway

Sat 2/7

6:40 am-12:40 pm

1 stop5h 00m

$217

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 Grand Rapids 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 day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Grand Rapids. The lowest ticket price found for a Tuesday departure recently was $391. 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 Grand Rapids because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $457.

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

Flying to Chicago Midway Airport from Grand Rapids in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $393 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $476. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Grand Rapids Gerald R. Ford Intl to Chicago Midway flight route?

Fly from Grand Rapids Gerald R. Ford Intl to Chicago Midway for the best Grand Rapids Gerald R. Ford Intl - Chicago Midway flight prices

What cabin class options are available on Grand Rapids Gerald R. Ford Intl to Chicago Midway flights?

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

When to book flights from Grand Rapids to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Grand Rapids to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Grand Rapids to Chicago Midway Airport (GRR to MDW) flight deals and tips

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

Best Price Found

$143

Fastest flight time

1h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Grand Rapids in the past 72 hours is $143. The best round-trip flight deal from Grand Rapids to Chicago Midway Airport found on momondo in the last 72 hours is $358.
The fastest flight from Grand Rapids to Chicago Midway Airport takes 1h 05m
Direct flights go from Grand Rapids to Chicago Midway Airport every day.
Search flight deals

  • How far is Grand Rapids Gerald R. Ford Intl to Chicago Midway by plane?

    Grand Rapids Gerald R. Ford Intl and Chicago Midway are 133.6 mi apart from one another. Typically, this will take 1h 00m by plane in normal conditions.

  • When did momondo last update prices for flights from Grand Rapids Gerald R. Ford Intl Airport to Chicago Midway Airport?

    Prices for flights from Grand Rapids Gerald R. Ford Intl Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Grand Rapids Gerald R. Ford Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Grand Rapids Gerald R. Ford Intl Airport 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 Grand Rapids Gerald R. Ford Intl Airport to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Grand Rapids to Chicago Midway Airport?

  • What is the most popular airline from Grand Rapids to Chicago Midway Airport?

Best airlines flying from Grand Rapids to Chicago Midway Airport

Compare and see reviews for airlines that fly from Grand Rapids to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $97Free CancellationRating
8.0
4,250 reviews
Search Southwest flights

  • Southwest Flights From Grand Rapids to Chicago Midway Airport

    Southwest operates around 10 flights from Grand Rapids to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $275, but momondo users have found Southwest deals from Grand Rapids to Chicago Midway Airport from as low as $97 round-trip. Southwest has been scored 8.0/10 in 4,250 reviews.

Traveling to a place near Chicago?

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

Why use momondo?

Why should I use momondo to find a flight deal from Grand Rapids to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Grand Rapids to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Grand Rapids to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Grand Rapids with this policy.

How can momondo help me find flights from Grand Rapids to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Grand Rapids.

I’m not ready to book a flight from Grand Rapids 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 Grand Rapids and alert you when they change.

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