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.
$39+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
jun. 17 — jun. 241
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 junio 12, 2025.
Round-trip from | $97 (Southwest) |
|---|---|
One-way from | $39 (Southwest) |
Popular in | February |
Cheapest in | October |
Average price | $373 |
Good round-trip deal | $355 or less |
Good one-way deal | $172 or less |
Find flight deals from Grand Rapids to Chicago
Cheapest flights from Grand Rapids to ChicagoExplore 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 junio 12, 2025.
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 junio 12, 2025.
This Southwest deal was found by Cheapflights users on 6/12. 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.
jue. 8/76:45 amGRR - MDW
Nonstop0h 55mSouthwest
lun. 8/119:15 pmMDW - GRR
Nonstop0h 55mSouthwest
Deal found 6/12![Southwest logo]()
$97
This American Airlines deal was found by Cheapflights users on 6/11. 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.
jue. 8/147:23 pmGRR - ORD
Nonstop1h 12mAmerican Airlines
lun. 8/186:59 amORD - GRR
Nonstop1h 03mAmerican Airlines
Deal found 6/11![American Airlines logo]()
$97
This United Airlines deal was found by Cheapflights users on 6/12. 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.
jue. 8/76:00 amGRR - ORD
Nonstop1h 12mUnited Airlines
lun. 8/119:50 pmORD - GRR
Nonstop1h 05mUnited Airlines
Deal found 6/12![United Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 6/10. 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.
jue. 8/145:30 amGRR - ORD
1 stop3h 34mDelta
lun. 8/187:00 pmORD - GRR
1 stop3h 46mDelta
Deal found 6/10![Delta logo]()
$177
This Mytrip deal was found by Cheapflights users on 6/12. 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.
jue. 7/109:59 pmGRR - ORD
1 stop24h 31mMultiple Airlines
jue. 7/175:05 amORD - GRR
2 stops32h 45mMultiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 6/11. 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.
sáb. 8/25:30 amGRR - MDW
1 stop4h 14mDelta
lun. 8/46:20 pmMDW - GRR
1 stop4h 26mDelta
Deal found 6/11![Delta logo]()
$254
This Mytrip deal was found by Cheapflights users on 6/11. 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.
jue. 7/101:46 pmGRR - MDW
1 stop19h 36mAllegiant Air
vie. 7/1110:31 amMDW - GRR
2 stops21h 22mAllegiant Air
Deal found 6/11![Allegiant Air logo]()
$283
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/17:11 pmGRR - ORD
1 stop13h 56mFrontier
vie. 8/296:00 amORD - GRR
1 stop12h 39mFrontier
Deal found 6/12![Frontier logo]()
$294
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/712:03 pmGRR - MDW
1 stop12h 14mFrontier
lun. 8/118:35 amMDW - GRR
1 stop8h 50mFrontier
Deal found 6/12![Frontier logo]()
$312
This Southwest deal was found by Cheapflights users on 6/9. 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.
mié. 6/255:35 amGRR - ORD
1 stop7h 15mSouthwest
mié. 6/251:50 pmORD - GRR
1 stop7h 10mSouthwest
Deal found 6/9![Southwest logo]()
$432
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 junio 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
jue. 8/7
6:45 am-6:40 am
Nonstop0h 55m
Chicago Midway
lun. 8/11
9:15 pm-11:10 pm
Nonstop0h 55m
$97
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
jue. 8/14
7:23 pm-7:35 pm
Nonstop1h 12m
Chicago O'Hare Intl
lun. 8/18
6:59 am-9:02 am
Nonstop1h 03m
$97
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
jue. 8/7
6:00 am-6:12 am
Nonstop1h 12m
Chicago O'Hare Intl
lun. 8/11
9:50 pm-11:55 pm
Nonstop1h 05m
$158
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
jue. 8/14
5:30 am-8:04 am
1 stop3h 34m
Chicago O'Hare Intl
lun. 8/18
7:00 pm-11:46 pm
1 stop3h 46m
$177
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
jue. 7/10
9:59 pm-9:30 pm
1 stop24h 31m
Chicago O'Hare Intl
jue. 7/17
5:05 am-2:50 pm
2 stops32h 45m
$220
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
sáb. 8/2
5:30 am-8:44 am
1 stop4h 14m
Chicago Midway
lun. 8/4
6:20 pm-11:46 pm
1 stop4h 26m
$254
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
jue. 7/10
1:46 pm-8:22 am
1 stop19h 36m
Chicago Midway
vie. 7/11
10:31 am-8:53 am
2 stops21h 22m
$283
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
vie. 8/1
7:11 pm-8:07 am
1 stop13h 56m
Chicago O'Hare Intl
vie. 8/29
6:00 am-7:39 pm
1 stop12h 39m
$294
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
jue. 8/7
12:03 pm-11:17 pm
1 stop12h 14m
Chicago Midway
lun. 8/11
8:35 am-6:25 pm
1 stop8h 50m
$312
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
mié. 6/25
5:35 am-11:50 am
1 stop7h 15m
Chicago O'Hare Intl
mié. 6/25
1:50 pm-10:00 pm
1 stop7h 10m
$432
Showing 1-10 of 21 results
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 Airlines
![Southwest]()
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.
Our travel experts
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 junio 12, 2025.
Unlike at noon, when flights are generally more expensive, you can save up to 26% 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 June 8, 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 junio 12, 2025.
The most flights from GRR to CHI are scheduled on a Wednesday (50 on average). You will have fewer flight options on Saturday, 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 junio 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.
Food
7.1
Boarding
8.2
Entertainment
7.6
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Boarding
8.2
Entertainment
7.6
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Boarding
8.2
Entertainment
7.6
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Boarding
8.2
Entertainment
7.6
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Boarding
8.2
Entertainment
7.6
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Boarding
8.2
Entertainment
7.6
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
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.
Traveling to a place near Grand Rapids?
Book flights to Grand Rapids if you plan to visit one of these locationsMerrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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.
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 junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$105 | Average$263 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$121 | Average$275 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$122 | Average$295 | FlexibilityNo cancel fee | On-time63% |