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$49+ 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

October

Average price

$205

Good round-trip deal

$318 or less

Good one-way deal

$153 or less
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. 18% potential increase in price ($68 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 September 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 10/96:05 pmGRR - MDW
Nonstop1h 05mSouthwest
Mon 10/139:30 amMDW - GRR
Nonstop0h 55mSouthwest
Deal found 9/15$97
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Mon 10/276:00 amGRR - ORD
Nonstop1h 12mAmerican Airlines
Wed 11/129:52 amORD - GRR
Nonstop1h 10mAmerican Airlines
Deal found 9/13$97
This American Airlines deal was found by Cheapflights users on 9/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:20 amGRR - ORD
Nonstop1h 10mAmerican Airlines
Mon 10/139:40 pmORD - GRR
Nonstop1h 05mAmerican Airlines
Deal found 9/12$98
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:39 pmGRR - ORD
Nonstop1h 11mUnited Airlines
Mon 10/138:05 pmORD - GRR
Nonstop1h 08mUnited Airlines
Deal found 9/12$115
This American Airlines deal was found by Cheapflights users on 9/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:40 amGRR - ORD
Nonstop1h 17mAmerican Airlines
Sun 11/167:09 amORD - GRR
Nonstop1h 00mAmerican Airlines
Deal found 9/12$133
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/106:00 amGRR - ORD
Nonstop1h 05mAmerican Airlines
Mon 10/139:40 pmORD - GRR
Nonstop1h 05mAmerican Airlines
Deal found 9/15$134
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 11/102:01 pmGRR - ORD
Nonstop1h 19mAmerican Airlines
Sat 11/226:59 amORD - GRR
Nonstop0h 59mAmerican Airlines
Deal found 9/14$157
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:20 pmGRR - ORD
1 stop8h 39mFrontier
Fri 10/310:42 amORD - GRR
1 stop7h 56mFrontier
Deal found 9/14$161
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 10/106:00 amGRR - ORD
Nonstop1h 05mAmerican Airlines
Fri 10/179:40 pmORD - GRR
Nonstop1h 05mAmerican Airlines
Deal found 9/13$171
This Southwest deal was found by Cheapflights users on 9/14. 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 10/223:55 pmGRR - MDW
1 stop5h 55mSouthwest
Sat 10/259:55 amMDW - GRR
Nonstop0h 50mSouthwest
Deal found 9/14$176
This Delta deal was found by Cheapflights users on 9/13. 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 10/282:06 pmGRR - ORD
1 stop3h 05mDelta
Tue 11/48:55 amORD - GRR
1 stop5h 34mDelta
Deal found 9/13$177
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2211:56 amGRR - ORD
1 stop6h 30mMultiple Airlines
Thu 9/2512:53 pmORD - GRR
1 stop26h 01mMultiple Airlines
Deal found 9/13$188

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 September 15, 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

Wed 10/22

5:00 pm-5:05 pm

Nonstop1h 05m

Chicago Midway

Sat 10/25

9:55 am-11:45 am

Nonstop0h 50m

$97

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 10/9

5:33 pm-5:44 pm

Nonstop1h 11m

Chicago O'Hare Intl

Sat 10/11

6:59 am-8:59 am

Nonstop1h 00m

$97

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

$97

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Mon 10/6

6:39 pm-6:50 pm

Nonstop1h 11m

Chicago O'Hare Intl

Mon 10/13

8:05 pm-10:13 pm

Nonstop1h 08m

$115

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Mon 11/10

2:01 pm-2:20 pm

Nonstop1h 19m

Chicago O'Hare Intl

Sat 11/22

6:59 am-8:58 am

Nonstop0h 59m

$157

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 10/2

4:20 pm-11:59 pm

1 stop8h 39m

Chicago O'Hare Intl

Fri 10/3

10:42 am-7:38 pm

1 stop7h 56m

$161

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Tue 10/28

2:06 pm-4:11 pm

1 stop3h 05m

Chicago O'Hare Intl

Tue 11/4

8:55 am-3:29 pm

1 stop5h 34m

$177

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Sat 11/1

2:06 pm-4:11 pm

1 stop3h 05m

Chicago O'Hare Intl

Tue 11/4

8:55 am-3:29 pm

1 stop5h 34m

$177

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

$208

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Mon 10/13

5:30 am-7:50 am

1 stop3h 20m

Chicago O'Hare Intl

Tue 10/14

8:55 am-1:26 pm

1 stop3h 31m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 39 results
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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 September 15, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 28% 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 September 14, 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 September 15, 2025.

The most flights from GRR to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (30 on average).

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 September 15, 2025.
See what other customers who have flown with Southwest, 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.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 45 outbound flights to Chicago per day.

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

    For as low as $97, Southwest can have you in Chicago from Grand Rapids in 1h 05m. Airlines will cover a distance of 136 mi. Most flights are nonstop.

  • 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. Other airlines that can offer you cheap pricing are Southwest, from $97, and United Airlines, from $114. These flights start at 69% lower than the current average price 3 months from now.

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

    $49 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $49 and $49, 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 Japan Airlines (80%), Envoy Air (77%) and United Airlines (75%).

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

    While on average a flight from Grand Rapids to Chicago is generally $793, our data shows the cheapest flight currently is $105. When looking at the most popular route, (Grand Rapids Gerald R. Ford Intl - Chicago O'Hare Intl), you can expect to pay $97 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$91Average$260FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$114Average$275FlexibilityNo cancel feeOn-time69%

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