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Cheap flights from Grand Rapids to Chicago from $85

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 9/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Grand Rapids to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:05 pm - 5:10 pm
GRR
-
MDW
1h 05mnonstop
Southwest Logo
1:05 pm - 3:00 pm
MDW
-
GRR
0h 55mnonstop
$169Southwest
Wed, Oct 7 - Tue, Oct 13
Southwest Logo
4:55 pm - 5:05 pm
GRR
-
MDW
1h 10mnonstop
Southwest Logo
7:30 am - 1:35 pm
MDW
-
GRR
5h 05m
1 stop
$180Southwest
Thu, Aug 20 - Thu, Aug 27
Delta Logo
3:37 pm - 6:05 pm
GRR
-
MDW
3h 28m
1 stop
Delta Logo
9:29 am - 1:19 pm
MDW
-
GRR
2h 50m
1 stop
$189Delta
Wed, Oct 7 - Tue, Oct 13
Southwest Logo
3:30 pm - 9:00 pm
GRR
-
MDW
6h 30m
1 stop
Southwest Logo
7:30 am - 1:35 pm
MDW
-
GRR
5h 05m
1 stop
$190Southwest
Thu, Aug 20 - Thu, Aug 27
Southwest Logo
12:55 pm - 1:00 pm
GRR
-
MDW
1h 05mnonstop
Southwest Logo
8:50 pm - 10:50 pm
MDW
-
GRR
1h 00mnonstop
$200Southwest
Fri, Aug 28 - Tue, Sep 1
Southwest Logo
3:30 pm - 9:00 pm
GRR
-
MDW
6h 30m
1 stop
Southwest Logo
10:05 am - 12:00 pm
MDW
-
GRR
0h 55mnonstop
$210Southwest
Fri, Aug 28 - Tue, Sep 1
Southwest Logo
12:55 pm - 1:00 pm
GRR
-
MDW
1h 05mnonstop
Southwest Logo
10:20 am - 12:15 pm
MDW
-
GRR
0h 55mnonstop
$216Southwest
Thu, Aug 20 - Thu, Aug 27
Southwest Logo
3:30 pm - 9:00 pm
GRR
-
MDW
6h 30m
1 stop
Southwest Logo
6:30 am - 1:00 pm
MDW
-
GRR
5h 30m
1 stop
$220Southwest
Fri, Aug 28 - Tue, Sep 1
Southwest Logo
5:45 am - 9:30 am
GRR
-
MDW
4h 45m
1 stop
Southwest Logo
10:20 am - 12:15 pm
MDW
-
GRR
0h 55mnonstop
$226Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
4:55 pm - 5:05 pm
GRR
-
MDW
1h 10mnonstop
Southwest Logo
8:55 pm - 10:55 pm
MDW
-
GRR
1h 00mnonstop
$230Southwest
Fri, Aug 21 - Fri, Aug 28

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Southwest flights from Grand Rapids to Chicago Midway Airport

Our best Southwest deals on Grand Rapids to Chicago Midway Airport flight tickets
Southwest
Oct 5
GRR1:20 pmGrand Rapids Gerald R. Ford Intl
1h 05m
MDW1:25 pmChicago Midway
Oct 10
MDW10:25 amChicago Midway
0h 55m
GRR12:20 pmGrand Rapids Gerald R. Ford Intl
$169
Southwest
Oct 5
GRR6:45 amGrand Rapids Gerald R. Ford Intl
1h 00m
MDW6:45 amChicago Midway
Oct 10
MDW6:55 amChicago Midway
5h 20m
1 stop
GRR1:15 pmGrand Rapids Gerald R. Ford Intl
$179
Southwest
Aug 20
GRR4:55 pmGrand Rapids Gerald R. Ford Intl
1h 10m
MDW5:05 pmChicago Midway
Aug 27
MDW7:30 amChicago Midway
5h 05m
1 stop
GRR1:35 pmGrand Rapids Gerald R. Ford Intl
$180

Delta flights from Grand Rapids to Chicago Midway Airport

Our best Delta deals on Grand Rapids to Chicago Midway Airport flight tickets
Delta
Sep 14
GRR4:00 pmGrand Rapids Gerald R. Ford Intl
3h 33m
1 stop
MDW6:33 pmChicago Midway
Sep 16
MDW9:29 amChicago Midway
4h 29m
1 stop
GRR2:58 pmGrand Rapids Gerald R. Ford Intl
$274
Delta
Jul 10
GRR2:35 pmGrand Rapids Gerald R. Ford Intl
4h 50m
1 stop
MDW6:25 pmChicago Midway
Jul 13
MDW1:18 pmChicago Midway
4h 43m
1 stop
GRR7:01 pmGrand Rapids Gerald R. Ford Intl
$541
Delta
Jul 15
GRR8:15 amGrand Rapids Gerald R. Ford Intl
5h 23m
1 stop
MDW12:38 pmChicago Midway
Jul 16
MDW6:58 pmChicago Midway
3h 57m
1 stop
GRR11:55 pmGrand Rapids Gerald R. Ford Intl
$1,119

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 July 9, 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
Quickest round-trip

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 10/7

5:05 pm-5:10 pm

Nonstop1h 05m

Chicago Midway

Tue 10/13

1:05 pm-3:00 pm

Nonstop0h 55m

$169

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 8/20

4:55 pm-5:05 pm

Nonstop1h 10m

Chicago Midway

Thu 8/27

7:30 am-1:35 pm

1 stop5h 05m

$180

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 10/7

3:37 pm-6:05 pm

1 stop3h 28m

Chicago Midway

Tue 10/13

9:29 am-1:19 pm

1 stop2h 50m

$189

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 8/20

3:30 pm-9:00 pm

1 stop6h 30m

Chicago Midway

Thu 8/27

7:30 am-1:35 pm

1 stop5h 05m

$190

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Fri 8/28

12:55 pm-1:00 pm

Nonstop1h 05m

Chicago Midway

Tue 9/1

8:50 pm-10:50 pm

Nonstop1h 00m

$200

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Fri 8/28

3:30 pm-9:00 pm

1 stop6h 30m

Chicago Midway

Tue 9/1

10:05 am-12:00 pm

Nonstop0h 55m

$210

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 8/20

12:55 pm-1:00 pm

Nonstop1h 05m

Chicago Midway

Thu 8/27

10:20 am-12:15 pm

Nonstop0h 55m

$216

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Fri 8/28

3:30 pm-9:00 pm

1 stop6h 30m

Chicago Midway

Tue 9/1

6:30 am-1:00 pm

1 stop5h 30m

$220

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 8/13

5:45 am-9:30 am

1 stop4h 45m

Chicago Midway

Mon 8/17

10:20 am-12:15 pm

Nonstop0h 55m

$226

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Fri 8/21

4:55 pm-5:05 pm

Nonstop1h 10m

Chicago Midway

Fri 8/28

8:55 pm-10:55 pm

Nonstop1h 00m

$230

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 $410. 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, Monday 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 $493.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $406 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $465. 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 to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Grand Rapids to Chicago Midway Airport 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 Grand Rapids to Chicago Midway Airport flights?

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

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

$213

Fastest flight time

1h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Grand Rapids in the past 72 hours is $213. The best round-trip flight deal from Grand Rapids to Chicago Midway Airport found on momondo in the last 72 hours is $405.
The fastest flight from Grand Rapids to Chicago Midway Airport takes 1h 00m
Direct flights go from Grand Rapids to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Grand Rapids to Chicago Midway Airport

  • 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 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?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Valparaiso
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Chesterton
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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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