Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Grand Rapids to Chicago from $49

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 11/18. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Grand Rapids to Chicago

Cheap round-trip flights

Southwest Logo
6:05 pm - 6:10 pmGRR-MDW
1h 05mnonstop
Southwest Logo
9:40 pm - 11:35 pmMDW-GRR
0h 55mnonstop
$97Southwest
Find Deal
Thu, Oct 9 - Mon, Oct 13
Southwest Logo
12:10 pm - 12:10 pmGRR-MDW
1h 00mnonstop
Southwest Logo
5:50 am - 2:25 pmMDW-GRR
7h 35m1 stop
$113Southwest
Find Deal
Mon, Oct 20 - Thu, Oct 23
Delta Logo
2:06 pm - 5:55 pmGRR-MDW
4h 49m1 stop
Delta Logo
9:35 am - 3:29 pmMDW-GRR
4h 54m1 stop
$177Delta
Find Deal
Sat, Nov 1 - Tue, Nov 4
Southwest Logo
3:00 pm - 8:35 pmGRR-MDW
6h 35m1 stop
Southwest Logo
5:50 am - 2:25 pmMDW-GRR
7h 35m1 stop
$189Southwest
Find Deal
Thu, Oct 23 - Thu, Oct 30
Southwest Logo
6:05 pm - 6:10 pmGRR-MDW
1h 05mnonstop
Southwest Logo
9:30 am - 11:25 amMDW-GRR
0h 55mnonstop
$201Southwest
Find Deal
Thu, Oct 9 - Mon, Oct 13
Delta Logo
2:17 pm - 5:20 pmGRR-MDW
4h 03m1 stop
Delta Logo
9:30 am - 3:17 pmMDW-GRR
4h 47m1 stop
$246Delta
Find Deal
Sun, Jan 4 - Mon, Jan 26
Multiple Airlines Logo
8:49 pm - 4:57 pmGRR-MDW
21h 08m2 stops
Multiple Airlines Logo
12:07 pm - 2:16 pmMDW-GRR
25h 09m1 stop
$259Multiple Airlines
Find Deal
Thu, Oct 23 - Thu, Oct 30
Multiple Airlines Logo
8:49 pm - 11:30 amGRR-MDW
15h 41m1 stop
Multiple Airlines Logo
12:07 pm - 11:46 amMDW-GRR
22h 39m1 stop
$262Multiple Airlines
Find Deal
Sun, Nov 2 - Sun, Nov 9
Frontier Logo
1:22 pm - 8:53 amGRR-MDW
20h 31m1 stop
Frontier Logo
10:13 am - 7:38 pmMDW-GRR
32h 25m2 stops
$280Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5
Frontier Logo
1:22 pm - 8:53 amGRR-MDW
20h 31m1 stop
Frontier Logo
7:15 am - 7:38 pmMDW-GRR
11h 23m2 stops
$331Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 6

Frontier flights from Grand Rapids to Chicago Midway Airport

Our best Frontier deals on Grand Rapids to Chicago Midway Airport flight tickets
Frontier
Oct 2
GRR1:22 pmGrand Rapids Gerald R. Ford Intl
20h 31m
1 stop
MDW8:53 amChicago Midway
Oct 5
MDW10:13 amChicago Midway
32h 25m
2 stops
GRR7:38 pmGrand Rapids Gerald R. Ford Intl
$280
Find similar
Frontier
Oct 2
GRR1:22 pmGrand Rapids Gerald R. Ford Intl
20h 31m
1 stop
MDW8:53 amChicago Midway
Oct 6
MDW7:15 amChicago Midway
11h 23m
2 stops
GRR7:38 pmGrand Rapids Gerald R. Ford Intl
$331
Find similar
Frontier
Oct 20
GRR9:10 amGrand Rapids Gerald R. Ford Intl
8h 10m
1 stop
MDW4:20 pmChicago Midway
Oct 23
MDW6:24 pmChicago Midway
23h 19m
2 stops
GRR6:43 pmGrand Rapids Gerald R. Ford Intl
$363
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
Nov 1
GRR2:06 pmGrand Rapids Gerald R. Ford Intl
4h 49m
1 stop
MDW5:55 pmChicago Midway
Nov 4
MDW9:35 amChicago Midway
4h 54m
1 stop
GRR3:29 pmGrand Rapids Gerald R. Ford Intl
$177
Find similar
Delta
Jan 4
GRR2:17 pmGrand Rapids Gerald R. Ford Intl
4h 03m
1 stop
MDW5:20 pmChicago Midway
Jan 26
MDW9:30 amChicago Midway
4h 47m
1 stop
GRR3:17 pmGrand Rapids Gerald R. Ford Intl
$246
Find similar
Delta
Nov 14
GRR5:23 amGrand Rapids Gerald R. Ford Intl
4h 29m
1 stop
MDW8:52 amChicago Midway
Nov 16
MDW6:48 pmChicago Midway
4h 11m
1 stop
GRR11:59 pmGrand Rapids Gerald R. Ford Intl
$307
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 September 19, 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 10/9

6:05 pm-6:10 pm

Nonstop1h 05m

Chicago Midway

Mon 10/13

9:40 pm-11:35 pm

Nonstop0h 55m

$97

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Mon 10/20

12:10 pm-12:10 pm

Nonstop1h 00m

Chicago Midway

Thu 10/23

5:50 am-2:25 pm

1 stop7h 35m

$113

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 11/1

2:06 pm-5:55 pm

1 stop4h 49m

Chicago Midway

Tue 11/4

9:35 am-3:29 pm

1 stop4h 54m

$177

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 10/23

3:00 pm-8:35 pm

1 stop6h 35m

Chicago Midway

Thu 10/30

5:50 am-2:25 pm

1 stop7h 35m

$189

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 10/9

6:05 pm-6:10 pm

Nonstop1h 05m

Chicago Midway

Mon 10/13

9:30 am-11:25 am

Nonstop0h 55m

$201

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sun 1/4

2:17 pm-5:20 pm

1 stop4h 03m

Chicago Midway

Mon 1/26

9:30 am-3:17 pm

1 stop4h 47m

$246

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 10/23

8:49 pm-4:57 pm

2 stops21h 08m

Chicago Midway

Thu 10/30

12:07 pm-2:16 pm

1 stop25h 09m

$259

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sun 11/2

8:49 pm-11:30 am

1 stop15h 41m

Chicago Midway

Sun 11/9

12:07 pm-11:46 am

1 stop22h 39m

$262

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 10/2

1:22 pm-8:53 am

1 stop20h 31m

Chicago Midway

Sun 10/5

10:13 am-7:38 pm

2 stops32h 25m

$280

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 10/2

1:22 pm-8:53 am

1 stop20h 31m

Chicago Midway

Mon 10/6

7:15 am-7:38 pm

2 stops11h 23m

$331

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $404. 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 $458.

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 $397 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $482. 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

$153

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 $153. The best round-trip flight deal from Grand Rapids to Chicago Midway Airport found on momondo in the last 72 hours is $318.
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

  • 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
4,242 reviews
Search Southwest flights

  • Southwest Flights From Grand Rapids to Chicago Midway Airport

    Southwest operates around 15 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 4,242 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 10/19
Sun 10/26
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago