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$79+ Cheap flights from Grand Rapids (GRR) to Chicago (CHI)

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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
Jun 26 — Jul 31
Fri 6/26
Fri 7/3
1 adult, Economy
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Cheap flight deals from Grand Rapids to Chicago

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

This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 6/1612:40 pm
GRR
-
MDW
Nonstop1h 05m
Southwest
Wed 6/179:55 pm
MDW
-
GRR
Nonstop0h 55m
Southwest
Deal found 5/26$157
This American Airlines deal was found by Cheapflights users on 5/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:00 am
GRR
-
ORD
Nonstop1h 13m
American Airlines
Tue 6/3010:30 pm
ORD
-
GRR
Nonstop1h 00m
American Airlines
Deal found 5/25$157
This Southwest deal was found by Cheapflights users on 5/25. 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.
Wed 8/197:15 am
GRR
-
MDW
Nonstop1h 20m
Southwest
Sat 8/226:15 pm
MDW
-
GRR
Nonstop0h 55m
Southwest
Deal found 5/25$174
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:10 pm
GRR
-
ORD
Nonstop1h 21m
American Airlines
Tue 9/2911:58 am
ORD
-
GRR
Nonstop1h 14m
American Airlines
Deal found 5/26$174
This Delta deal was found by Cheapflights users on 5/26. 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.
Tue 6/162:48 pm
GRR
-
MDW
1 stop4h 43m
Delta
Wed 6/179:17 am
MDW
-
GRR
1 stop3h 51m
Delta
Deal found 5/26$177
This Southwest deal was found by Cheapflights users on 5/22. 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.
Tue 7/211:55 pm
GRR
-
MDW
1 stop5h 00m
Southwest
Wed 7/229:55 pm
MDW
-
GRR
Nonstop1h 00m
Southwest
Deal found 5/22$187
This Southwest deal was found by Cheapflights users on 5/23. 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.
Thu 8/204:55 pm
GRR
-
MDW
Nonstop1h 10m
Southwest
Mon 8/2410:20 am
MDW
-
GRR
Nonstop0h 55m
Southwest
Deal found 5/23$191
This American Airlines deal was found by Cheapflights users on 5/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:33 am
GRR
-
ORD
Nonstop1h 27m
American Airlines
Mon 9/287:09 am
ORD
-
GRR
Nonstop1h 13m
American Airlines
Deal found 5/25$191
This Delta deal was found by Cheapflights users on 5/26. 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 9/268:25 am
GRR
-
MDW
1 stop5h 09m
Delta
Tue 9/299:30 am
MDW
-
GRR
1 stop3h 33m
Delta
Deal found 5/26$194
This Delta deal was found by Cheapflights users on 5/26. 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 9/268:25 am
GRR
-
ORD
1 stop5h 39m
Delta
Tue 9/299:00 am
ORD
-
GRR
1 stop4h 03m
Delta
Deal found 5/26$194
This Delta deal was found by Cheapflights users on 5/21. 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.
Tue 7/75:30 am
GRR
-
ORD
1 stop6h 07m
Delta
Wed 7/87:17 pm
ORD
-
GRR
1 stop3h 38m
Delta
Deal found 5/21$197
This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 6/234:40 pm
GRR
-
MDW
Nonstop1h 05m
Southwest
Tue 6/305:30 pm
MDW
-
GRR
1 stop4h 25m
Southwest
Deal found 5/26$202

Find flight deals from Grand Rapids to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Grand Rapids (GRR) to Chicago (CHI). 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 May 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

January

Cheapest in

October

Average price

$261

Good round-trip deal

$424 or less

Good one-way deal

$211 or less
Provider with most accurate pricing for Grand Rapids Gerald R. Ford Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Grand Rapids Gerald R. Ford Intl-Chicago (CHI) flights.
Search Deals
From Grand Rapids Gerald R. Ford Intl to Chicago (CHI)
Search Deals
One-way flight from Grand Rapids Gerald R. Ford Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($123 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Grand Rapids Gerald R. Ford Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Grand Rapids Gerald R. Ford Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Grand Rapids to Chicago 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 May 27, 2026.
Use the filters below to find and compare flights from Grand Rapids to Chicago 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

Tue 7/21

1:55 pm-5:55 pm

1 stop5h 00m

Chicago Midway

Wed 7/22

5:30 pm-11:00 pm

1 stop4h 30m

$197

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 8/20

5:30 am-7:56 am

1 stop3h 26m

Chicago O'Hare Intl

Mon 8/24

5:20 pm-11:55 pm

1 stop5h 35m

$211

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Tue 7/28

12:10 pm-4:23 pm

1 stop5h 13m

Chicago O'Hare Intl

Thu 7/30

7:05 am-1:55 pm

1 stop5h 50m

$215

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Wed 7/29

2:35 pm-6:29 pm

1 stop4h 54m

Chicago O'Hare Intl

Fri 7/31

5:18 pm-11:55 pm

1 stop5h 37m

$238
Quickest round-trip

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 6/17

12:40 pm-12:45 pm

Nonstop1h 05m

Chicago Midway

Tue 6/23

10:05 am-12:00 pm

Nonstop0h 55m

$246

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 7/2

2:00 pm-6:31 pm

1 stop5h 31m

Chicago Midway

Sun 7/5

6:58 pm-11:57 pm

1 stop3h 59m

$275

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 7/2

8:15 am-1:00 pm

1 stop5h 45m

Chicago O'Hare Intl

Sun 7/5

1:40 pm-7:06 pm

1 stop4h 26m

$275

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 7/2

2:45 pm-8:20 pm

2 stops6h 35m

Chicago Midway

Mon 7/20

9:25 pm-11:25 pm

Nonstop1h 00m

$278

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 7/29

5:30 am-9:08 am

1 stop4h 38m

Chicago Midway

Fri 7/31

6:58 pm-11:55 pm

1 stop3h 57m

$279

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Sat 6/27

3:41 pm-8:31 pm

1 stop5h 50m

Chicago O'Hare Intl

Sat 7/11

7:05 am-11:21 am

1 stop3h 16m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/26

Showing 1-10 of 38 resultsSorted by cheapest first
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Compare providers for flights from Grand Rapids to Chicago

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 Chicago in May.
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 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Grand Rapids-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Grand Rapids-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

What is the cheapest month to book a flight from Grand Rapids to Chicago?

Currently, October is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $61). Flying from Grand Rapids to Chicago in July is currently the most expensive (average of $245). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

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

Unlike at noon, when flights are generally more expensive, you can save up to 18% on flights from Grand Rapids to Chicago by exploring options for tickets in the morning.

Weekly flight availability from Grand Rapids to Chicago

Explore weekly flight availability from Grand Rapids to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 27, 2026.

The most flights from GRR to CHI are scheduled on a Tuesday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

How much does it cost to fly round-trip from Grand Rapids to Chicago?

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

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

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 27, 2026.
See what other customers who have flown with United Airlines and American Airlines from Grand Rapids to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,751 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,751 reviews
United Airlines
7.4
Good
9,751 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,640 reviews
United Airlines
7.4
Good
9,751 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Grand Rapids to Chicago. 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?

    Grand Rapids Gerald R. Ford Intl (GRR), located 9.2 mi from the city center, is the airport you fly out of when you book flights from Grand Rapids to Chicago. 2 airlines have flights from Gerald R. Ford Intl to Chicago on a regular basis. Booking flights from Grand Rapids Gerald R. Ford Intl to Chicago should not be difficult; the airport handles an average of 43 outbound flights to Chicago per day.

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

    For as low as $211, Southwest can have you in Chicago from Grand Rapids in 3h 26m. Airlines will cover a distance of 136 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Grand Rapids to Chicago round-trip?

    Cheapflights users have booked flights from Grand Rapids to Chicago round-trip from $91. Another airline that can offer you cheap pricing is United Airlines. These flights start at 70% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Grand Rapids to Chicago one-way?

    $48 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Southwest, with prices starting from $48 and $121, respectively.

  • What are the most reliable airlines from Grand Rapids to Chicago?

    The top 3 most reliable airlines when flying from Grand Rapids to Chicago are Aer Lingus (78%), Air Canada (75%) and American Airlines (74%).

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

    While on average a flight from Grand Rapids to Chicago is generally $1,031, our data shows the cheapest flight currently is $165. When looking at the most popular route, (Grand Rapids Gerald R. Ford Intl - Chicago O'Hare Intl), you can expect to pay $157 for that flight.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Grand Rapids to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $61). Flying from Grand Rapids to Chicago in July is currently the most expensive (average of $245). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

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

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Top 2 airlines flying from Grand Rapids to Chicago

Discover the top 2 airlines that operate flights from Grand Rapids to Chicago. 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 May 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$91Average$263FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$107Average$266FlexibilityNo cancel feeOn-time69%

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