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$89+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
May 17 — May 241
Sat 5/17
Sat 5/24
1 adult, Economy
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Cheap 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 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$215
(American Airlines)

One-way from

$101
(Southwest)

Popular in

February

Cheapest in

August

Average price

$273

Good round-trip deal

$349 or less

Good one-way deal

$165 or less
Provider with most accurate pricing for Grand Rapids Gerald R. Ford Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Grand Rapids Gerald R. Ford Intl-Chicago (CHI) flights.
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From Grand Rapids Gerald R. Ford Intl to Chicago (CHI)
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One-way flight from Grand Rapids Gerald R. Ford Intl to Chicago (CHI)
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Highest demand for flights based on searches. 20% potential increase in price ($76 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Grand Rapids Gerald R. Ford Intl to Chicago (CHI).
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Price to beat on a one-way flight from Grand Rapids Gerald R. Ford Intl to Chicago (CHI).
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Find 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 12, 2025.

This Southwest deal was found by Cheapflights users on 5/12. 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.
Sat 5/247:00 amGRR - MDW
Nonstop1h 00mSouthwest
Sun 5/2511:10 amMDW - GRR
Nonstop0h 50mSouthwest
Deal found 5/12$215
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Wed 5/286:00 amGRR - ORD
Nonstop1h 10mAmerican Airlines
Sat 5/311:10 pmORD - GRR
Nonstop0h 59mAmerican Airlines
Deal found 5/11$215
This Delta deal was found by Cheapflights users on 5/11. 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.
Wed 6/252:20 pmGRR - MDW
1 stop5h 21mDelta
Wed 7/26:20 pmMDW - GRR
1 stop4h 26mDelta
Deal found 5/11$233
This Delta deal was found by Cheapflights users on 5/11. 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.
Wed 5/283:34 pmGRR - ORD
1 stop4h 03mDelta
Sat 5/317:10 amORD - GRR
1 stop5h 04mDelta
Deal found 5/11$235
This Mytrip deal was found by Cheapflights users on 5/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/137:39 pmGRR - MDW
1 stop13h 43mAllegiant Air
Mon 7/1410:31 amMDW - GRR
2 stops35h 01mAllegiant Air
Deal found 5/12$265
This United Airlines deal was found by Cheapflights users on 5/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1012:55 pmGRR - ORD
Nonstop1h 14mUnited Airlines
Tue 6/179:05 amORD - GRR
Nonstop1h 12mUnited Airlines
Deal found 5/11$285
This Southwest deal was found by Cheapflights users on 5/11. 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.
Mon 6/95:40 amGRR - ORD
1 stop8h 25mSouthwest
Wed 6/111:50 pmORD - GRR
1 stop7h 10mSouthwest
Deal found 5/11$303
This Mytrip deal was found by Cheapflights users on 5/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/37:14 pmGRR - ORD
1 stop18h 37mMultiple Airlines
Sun 7/611:50 amORD - GRR
2 stops29h 24mMultiple Airlines
Deal found 5/11$352

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 12, 2025.
Use the filters below to find and compare flights from Grand Rapids to Chicago that are best for you.

Fly from

Grand Rapids

Fly to

Chicago

Route

Depart

Return

Price

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 5/24

7:00 am-7:00 am

Nonstop1h 00m

Chicago Midway

Sun 5/25

11:10 am-1:00 pm

Nonstop0h 50m

$215

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Sat 5/24

6:00 am-6:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Sun 5/25

2:54 pm-4:49 pm

Nonstop0h 55m

$215

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Sun 6/22

9:58 pm-3:33 pm

1 stop18h 35m

Chicago O'Hare Intl

Sat 6/28

9:28 pm-1:50 pm

1 stop15h 22m

$224

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 6/25

2:20 pm-6:41 pm

1 stop5h 21m

Chicago Midway

Wed 7/2

6:20 pm-11:46 pm

1 stop4h 26m

$233

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Sat 5/24

10:17 am-12:41 pm

1 stop3h 24m

Chicago O'Hare Intl

Sun 5/25

7:10 am-1:19 pm

1 stop5h 09m

$235

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sun 7/13

7:39 pm-8:22 am

1 stop13h 43m

Chicago Midway

Mon 7/14

10:31 am-10:32 pm

2 stops35h 01m

$265

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Tue 6/10

12:55 pm-1:09 pm

Nonstop1h 14m

Chicago O'Hare Intl

Tue 6/17

9:05 am-11:17 am

Nonstop1h 12m

$285

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Mon 6/9

5:40 am-1:05 pm

1 stop8h 25m

Chicago O'Hare Intl

Wed 6/11

1:50 pm-10:00 pm

1 stop7h 10m

$303

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Sun 7/13

9:59 pm-8:03 pm

1 stop23h 04m

$89

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 8/30

4:40 pm-4:40 pm

Nonstop1h 00m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

Showing 1-10 of 17 results
1
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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*2 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 Expedia the most. Expedia 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.

The best insider tips for Grand Rapids to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Grand Rapids to Chicago trip
Airlines
United Airlines

United's Economy Plus offers extra legroom, ideal for a comfortable short-haul flight.


Prepay for checked bags 24 hours before to save on fees.

Read more about United Airlinesby Harriet Baskas
Southwest

Enjoy free snacks and non-alcoholic drinks on board, enhancing your short flight experience.


Southwest offers two free checked bags, including oversized items like skis or golf clubs.

Read more about Southwestby Marisa Garcia
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more

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, August is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $245). Flying from Grand Rapids to Chicago in March is currently the most expensive (average of $321). 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 12, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 25% on flights from Grand Rapids to Chicago by exploring options for tickets in the morning.

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 11, 2025.

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

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 12, 2025.

The most flights from GRR to CHI are scheduled on a Friday (50 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (35 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 12, 2025.
To help decide which airline to fly from Grand Rapids to Chicago, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,724 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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. 3 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 42 outbound flights to Chicago per day.

  • 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 $215. Other airlines that can offer you cheap pricing are Southwest, from $225, and Delta, from $233. These flights start at 25% lower than the current average price 3 months from now.

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

    $101 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on American Airlines and Allegiant Air, with prices starting from $101 and $104, 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 Air Wisconsin (100%), Republic Airways (92%) and Envoy Air (85%).

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

    While on average a flight from Grand Rapids to Chicago is generally $788, our data shows the cheapest flight currently is $134. When looking at the most popular route, (Grand Rapids Gerald R. Ford Intl - Chicago O'Hare Intl), you can expect to pay $167 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, August is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $245). Flying from Grand Rapids to Chicago in March is currently the most expensive (average of $321). 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 Grand Rapids?

Book flights to Grand Rapids if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Grand Rapids to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Grand Rapids to Chicago

Discover the top 3 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$262FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$121Average$276FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$122Average$295FlexibilityNo cancel feeOn-time63%

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