HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$46+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Grand Rapids to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$94
(Southwest)

One-way from

$46
(Southwest)

Popular in

February

Cheapest in

October

Average price

$176

Good round-trip deal

$297 or less

Good one-way deal

$179 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. 17% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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

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 October 16, 2025.

This Southwest deal was found by Cheapflights users on 10/16. 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 11/205:00 pmGRR - MDW
Nonstop1h 15mSouthwest
Mon 11/249:30 amMDW - GRR
Nonstop0h 55mSouthwest
Deal found 10/16$94
This Southwest deal was found by Cheapflights users on 10/15. 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.
Wed 11/55:00 pmGRR - MDW
Nonstop1h 15mSouthwest
Thu 11/69:30 amMDW - GRR
Nonstop0h 55mSouthwest
Deal found 10/15$97
This United Airlines deal was found by Cheapflights users on 10/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:11 amGRR - ORD
Nonstop1h 19mUnited Airlines
Wed 11/59:30 pmORD - GRR
Nonstop1h 04mUnited Airlines
Deal found 10/15$97
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Wed 11/58:01 amGRR - ORD
Nonstop1h 24mAmerican Airlines
Wed 12/39:52 amORD - GRR
Nonstop1h 16mAmerican Airlines
Deal found 10/14$98
This Southwest deal was found by Cheapflights users on 10/15. 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.
Wed 12/245:00 pmGRR - MDW
Nonstop1h 15mSouthwest
Mon 1/55:05 amMDW - GRR
1 stop6h 40mSouthwest
Deal found 10/15$104
This Southwest deal was found by Cheapflights users on 10/16. 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 11/101:25 pmGRR - MDW
2 stops8h 05mSouthwest
Mon 11/1010:10 pmMDW - GRR
Nonstop0h 55mSouthwest
Deal found 10/16$112
This Southwest deal was found by Cheapflights users on 10/15. 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.
Tue 11/183:00 pmGRR - MDW
1 stop7h 05mSouthwest
Wed 11/196:40 amMDW - GRR
1 stop6h 30mSouthwest
Deal found 10/15$117
This United Airlines deal was found by Cheapflights users on 10/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/54:55 pmGRR - ORD
Nonstop1h 12mUnited Airlines
Wed 11/129:05 amORD - GRR
Nonstop1h 07mUnited Airlines
Deal found 10/14$157
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Tue 11/259:42 amGRR - ORD
Nonstop1h 09mAmerican Airlines
Tue 12/22:04 pmORD - GRR
Nonstop1h 09mAmerican Airlines
Deal found 10/14$166
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 11/157:05 amGRR - MDW
Nonstop1h 10mSouthwest
Sat 11/159:55 amMDW - GRR
Nonstop1h 00mSouthwest
Deal found 10/15$171
This United Airlines deal was found by Cheapflights users on 10/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:30 amGRR - ORD
Nonstop1h 12mUnited Airlines
Sat 11/156:11 pmORD - GRR
Nonstop1h 06mUnited Airlines
Deal found 10/15$171
This American Airlines deal was found by Cheapflights users on 10/16. 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 11/2011:56 amGRR - ORD
1 stop5h 09mAmerican Airlines
Mon 11/2410:05 pmORD - GRR
Nonstop0h 54mAmerican Airlines
Deal found 10/16$172

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 October 16, 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

Tue 11/18

5:00 pm-5:15 pm

Nonstop1h 15m

Chicago Midway

Wed 11/19

1:25 pm-3:20 pm

Nonstop0h 55m

$97

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Tue 11/18

4:24 pm-4:40 pm

Nonstop1h 16m

Chicago O'Hare Intl

Wed 11/19

9:58 am-12:08 pm

Nonstop1h 10m

$97

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Wed 11/5

7:30 am-7:42 am

Nonstop1h 12m

Chicago O'Hare Intl

Thu 11/6

9:30 pm-11:34 pm

Nonstop1h 04m

$97

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Mon 11/17

5:00 pm-5:15 pm

Nonstop1h 15m

Chicago Midway

Mon 11/17

8:40 pm-10:35 pm

Nonstop0h 55m

$97

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 12/17

5:00 pm-5:15 pm

Nonstop1h 15m

Chicago Midway

Wed 12/17

8:40 pm-10:35 pm

Nonstop0h 55m

$97

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 11/5

3:00 pm-9:05 pm

1 stop7h 05m

Chicago Midway

Thu 11/6

9:30 am-11:25 am

Nonstop0h 55m

$107

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Mon 11/10

1:25 pm-8:30 pm

2 stops8h 05m

Chicago Midway

Mon 11/10

10:10 pm-12:05 am

Nonstop0h 55m

$112

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 12/24

2:45 pm-9:05 pm

1 stop7h 20m

Chicago Midway

Mon 1/5

5:05 am-12:45 pm

1 stop6h 40m

$114

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 11/20

5:00 pm-5:15 pm

Nonstop1h 15m

Chicago Midway

Mon 11/24

5:05 am-12:45 pm

1 stop6h 40m

$144

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Mon 1/5

1:25 pm-8:30 pm

2 stops8h 05m

Chicago Midway

Mon 1/5

10:10 pm-12:05 am

Nonstop0h 55m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 44 results
1
2
3
...
5

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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, 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 October 16, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 21% 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 October 12, 2025.

Travelers seeking maximum savings on their Grand Rapids to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Wednesday at noon 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 October 16, 2025.

The most flights from GRR to CHI are scheduled on a Thursday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 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 October 16, 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

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

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

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

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
8,982 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

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
11,043 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

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 44 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 12m. 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 United Airlines, from $97, and Southwest, from $97. 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?

    $46 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 Delta, with prices starting from $49 and $79, 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 (85%), Envoy Air (80%) and Copa Airlines (76%).

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

    While on average a flight from Grand Rapids to Chicago is generally $975, 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Grand Rapids to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Detroit to O'Hare Intl flights
Detroit to Midway flights
Detroit to St. Louis flights
O'Hare Intl to St. Louis flights
Flint to O'Hare Intl flights
Muskegon to O'Hare Intl flights
Midway to St. Louis flights
Grand Rapids to O'Hare Intl flights
Traverse City to O'Hare Intl flights
Grand Rapids to St. Louis flights
Grand Rapids to Midway flights
Bay City to O'Hare Intl flights
O'Hare Intl to Peoria flights
Lansing to O'Hare Intl flights
Detroit to Moline flights
O'Hare Intl to Burlington flights
Bay City to Midway flights
Traverse City to Midway flights
Marquette to O'Hare Intl flights
Flint to St. Louis flights
South Bend to O'Hare Intl flights
O'Hare Intl to Evansville flights
Lansing to Midway flights
O'Hare Intl to Moline flights
Flint to Midway flights
O'Hare Intl to Springfield flights
Pellston to O'Hare Intl flights
South Bend to St. Louis flights
South Bend to Midway flights
Kalamazoo to O'Hare Intl flights
Kalamazoo to Midway flights
Bay City to St. Louis flights
O'Hare Intl to Decatur flights
Detroit to Peoria flights
Grand Rapids to Peoria flights
Lansing to St. Louis flights
Sault Ste. Marie to O'Hare Intl flights
O'Hare Intl to Champaign flights
O'Hare Intl to Bloomington flights
Traverse City to St. Louis flights
Detroit to Evansville flights
Flint to Peoria flights
Marquette to Midway flights
Escanaba to O'Hare Intl flights
Kalamazoo to St. Louis flights
O'Hare Intl to Paducah flights
Detroit to Bloomington flights
Sault Ste. Marie to Midway flights
Ironwood to O'Hare Intl flights

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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$91Average$263FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$97Average$275FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$97Average$226FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.