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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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$99
(American Airlines)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

October

Average price

$285

Good round-trip deal

$308 or less

Good one-way deal

$159 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. 16% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/5. 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 12/52:23 pmGRR - ORD
Nonstop1h 21mAmerican Airlines
Sun 12/710:00 pmORD - GRR
Nonstop0h 59mAmerican Airlines
Deal found 11/5$101
This Southwest deal was found by Cheapflights users on 11/6. 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 12/95:00 pmGRR - MDW
Nonstop1h 15mSouthwest
Tue 12/98:40 pmMDW - GRR
Nonstop0h 55mSouthwest
Deal found 11/6$117
This Delta deal was found by Cheapflights users on 11/6. 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 12/95:30 amGRR - MDW
1 stop4h 24mDelta
Tue 12/96:40 pmMDW - GRR
1 stop4h 14mDelta
Deal found 11/6$157
This Delta deal was found by Cheapflights users on 11/6. 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 12/95:30 amGRR - ORD
1 stop3h 34mDelta
Tue 12/96:00 pmORD - GRR
1 stop4h 54mDelta
Deal found 11/6$157
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Thu 12/412:56 pmGRR - ORD
Nonstop1h 19mUnited Airlines
Sun 12/77:35 pmORD - GRR
Nonstop1h 06mUnited Airlines
Deal found 11/6$161
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Thu 12/44:58 pmGRR - ORD
Nonstop1h 12mUnited Airlines
Thu 12/116:07 pmORD - GRR
Nonstop1h 06mUnited Airlines
Deal found 11/6$171
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/153:54 pmGRR - ORD
Nonstop1h 24mAmerican Airlines
Mon 12/2210:05 pmORD - GRR
Nonstop0h 54mAmerican Airlines
Deal found 11/5$183
This Delta deal was found by Cheapflights users on 11/6. 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.
Thu 12/113:37 pmGRR - ORD
1 stop5h 58mDelta
Mon 12/155:07 pmORD - GRR
1 stop5h 47mDelta
Deal found 11/6$191
This American Airlines deal was found by Cheapflights users on 11/6. 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 12/1712:38 pmGRR - ORD
Nonstop1h 21mAmerican Airlines
Fri 12/2610:05 pmORD - GRR
Nonstop0h 54mAmerican Airlines
Deal found 11/6$198
This Southwest deal was found by Cheapflights users on 11/5. 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.
Sun 12/76:10 pmGRR - MDW
Nonstop1h 05mSouthwest
Tue 12/98:40 pmMDW - GRR
Nonstop0h 55mSouthwest
Deal found 11/5$206
This Delta deal was found by Cheapflights users on 11/5. 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 12/65:30 amGRR - MDW
1 stop4h 19mDelta
Sat 12/61:14 pmMDW - GRR
1 stop3h 04mDelta
Deal found 11/5$223
This Delta deal was found by Cheapflights users on 11/6. 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.
Thu 12/43:37 pmGRR - MDW
1 stop3h 23mDelta
Thu 12/119:34 amMDW - GRR
1 stop2h 45mDelta
Deal found 11/6$225

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 November 6, 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 - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Sat 1/10

11:41 am-11:56 am

Nonstop1h 15m

Chicago O'Hare Intl

Sat 1/17

1:55 pm-3:55 pm

Nonstop1h 00m

$134

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Mon 12/15

5:00 pm-5:15 pm

Nonstop1h 15m

Chicago Midway

Wed 12/17

8:40 pm-10:35 pm

Nonstop0h 55m

$136

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Mon 12/15

11:47 am-12:05 pm

Nonstop1h 18m

Chicago O'Hare Intl

Tue 12/30

9:18 pm-11:30 pm

Nonstop1h 12m

$137

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 1/13

8:10 am-12:48 pm

1 stop5h 38m

Chicago Midway

Sat 1/17

1:28 pm-5:13 pm

1 stop2h 45m

$157

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Tue 12/9

5:30 am-8:04 am

1 stop3h 34m

Chicago O'Hare Intl

Tue 12/9

6:00 pm-11:54 pm

1 stop4h 54m

$157

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Tue 1/13

5:55 pm-9:04 pm

1 stop4h 09m

Chicago O'Hare Intl

Tue 1/20

1:58 pm-9:06 pm

1 stop6h 08m

$157

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 12/4

12:56 pm-1:15 pm

Nonstop1h 19m

Chicago O'Hare Intl

Sun 12/7

7:35 pm-9:41 pm

Nonstop1h 06m

$161

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Mon 12/15

5:00 pm-5:15 pm

Nonstop1h 15m

Chicago Midway

Thu 12/18

9:30 am-11:25 am

Nonstop0h 55m

$164

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Mon 12/15

3:37 pm-8:35 pm

1 stop5h 58m

Chicago O'Hare Intl

Tue 12/30

7:00 am-1:37 pm

1 stop5h 37m

$167

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 12/11

11:47 am-12:05 pm

Nonstop1h 18m

Chicago O'Hare Intl

Mon 12/15

9:05 am-11:12 am

Nonstop1h 07m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 41 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Grand Rapids-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, January is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $78). Flying from Grand Rapids to Chicago in July is currently the most expensive (average of $149). 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 November 6, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 22% 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 November 2, 2025.

Travelers seeking maximum savings on their Grand Rapids to Chicago flight should consider departing on Tuesday afternoons 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.

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 November 6, 2025.

The most flights from GRR to CHI are scheduled on a Thursday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).

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

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 November 6, 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
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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 39 outbound flights to Chicago per day.

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

    For as low as $134, United Airlines can have you in Chicago from Grand Rapids in 1h 15m. 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. Other airlines that can offer you cheap pricing are United Airlines, from $97, and Southwest, from $97. These flights start at 68% 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 $51 and $51, 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 Canada (86%), Iberia (80%) and Japan Airlines (80%).

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

    While on average a flight from Grand Rapids to Chicago is generally $728, our data shows the cheapest flight currently is $119. 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, January is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $78). Flying from Grand Rapids to Chicago in July is currently the most expensive (average of $149). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$91Average$264FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$97Average$274FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$97Average$226FlexibilityNo cancel feeOn-time63%

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