$120+ Cheap flights from Grand Rapids (GRR) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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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
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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 September 10, 2026.
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 10, 2026.
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 10/11:20 pm -
Nonstop1h 05m
Sat 10/310:25 am -
Nonstop0h 55m
Deal found 9/9![Southwest logo]()
$265
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:50 am -
Nonstop1h 18m
Sat 10/311:00 am -
Nonstop1h 09m
Deal found 9/9![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 9/7. 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 10/121:20 pm -
Nonstop1h 05m
Fri 10/239:40 am -
Nonstop0h 55m
Deal found 9/7![Southwest logo]()
$278
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:15 pm -
Nonstop1h 20m
Mon 10/269:50 pm -
Nonstop1h 08m
Deal found 9/9![United Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/198:46 pm -
Nonstop1h 44m
Wed 1/201:26 pm -
Nonstop1h 14m
Deal found 9/9![American Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 9/9. 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.
Tue 12/111:00 am -
Nonstop1h 15m
Tue 12/11:15 pm -
2 stops8h 10m
Deal found 9/9![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 9/7. 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 12/247:20 pm -
Nonstop1h 20m
Thu 1/71:25 pm -
1 stop7h 40m
Deal found 9/7![Southwest logo]()
$281
This Delta deal was found by Cheapflights users on 9/8. 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 10/15:30 am -
1 stop4h 37m
Sat 10/39:29 am -
1 stop4h 29m
Deal found 9/8![Delta logo]()
$285
This Delta deal was found by Cheapflights users on 9/8. 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 10/15:30 am -
1 stop3h 26m
Sat 10/38:55 am -
1 stop5h 03m
Deal found 9/8![Delta logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Fri 10/235:17 pm -
1 stop6h 22m
Wed 10/287:28 pm -
2 stops43h 59m
Deal found 9/8![Multiple Airlines logo]()
$292
This Southwest deal was found by Cheapflights users on 9/6. 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.
Thu 10/151:20 pm -
Nonstop1h 05m
Mon 10/199:45 pm -
Nonstop1h 00m
Deal found 9/6![Southwest logo]()
$293
This American Airlines deal was found by Cheapflights users on 9/4. 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 10/82:26 pm -
Nonstop1h 18m
Sat 10/1010:40 pm -
Nonstop1h 11m
Deal found 9/4![American Airlines logo]()
$293
Best flights from Grand Rapids to ChicagoDiscover carefully curated flight deals from Grand Rapids to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Grand Rapids to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This Southwest deal was found by Cheapflights users on 9/7. 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 10/102:45 pm -
Nonstop1h 05m
Mon 10/129:45 pm -
Nonstop1h 00m
Deal found 9/7![Southwest logo]()
$265
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:58 am -
Nonstop1h 23m
Wed 10/145:59 am -
Nonstop1h 12m
Deal found 9/9![United Airlines logo]()
$265
This American Airlines deal was found by Cheapflights users on 9/4. 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 10/82:26 pm -
Nonstop1h 18m
Sat 10/1010:40 pm -
Nonstop1h 11m
Deal found 9/4![American Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 9/5. 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.
Thu 12/177:40 am -
1 stop6h 21m
Wed 1/69:30 am -
1 stop3h 07m
Deal found 9/5![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 10/76:50 am -
Nonstop1h 00m
Wed 10/141:05 pm -
Nonstop0h 55m
Deal found 9/9![Southwest logo]()
$265
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:15 pm -
Nonstop1h 20m
Mon 10/269:50 pm -
Nonstop1h 08m
Deal found 9/9![United Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 9/9. 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.
Fri 10/236:45 am -
Nonstop1h 00m
Mon 10/269:45 pm -
Nonstop1h 00m
Deal found 9/9![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 9/5. 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.
Tue 12/1510:29 am -
1 stop3h 32m
Sat 1/91:00 pm -
1 stop3h 26m
Deal found 9/5![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:44 am -
Nonstop1h 15m
Sun 10/49:05 am -
Nonstop1h 17m
Deal found 9/9![United Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 9/5. 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.
Mon 12/143:51 pm -
1 stop3h 10m
Tue 1/55:59 pm -
1 stop3h 43m
Deal found 9/5![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 9/6. 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.
Thu 10/151:20 pm -
Nonstop1h 05m
Mon 10/197:25 am -
1 stop4h 15m
Deal found 9/6![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 9/4. 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 10/85:30 am -
1 stop3h 11m
Sat 10/107:00 am -
1 stop5h 23m
Deal found 9/4![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 9/5. 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.
Mon 1/41:25 pm -
Nonstop1h 20m
Mon 1/46:10 pm -
1 stop5h 10m
Deal found 9/5![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 9/8. 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 10/15:30 am -
1 stop3h 26m
Sun 10/47:30 pm -
1 stop3h 18m
Deal found 9/8![Delta logo]()
$348
This United Airlines deal was found by Cheapflights users on 9/7. 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 10/125:44 am -
Nonstop1h 15m
Wed 10/1411:00 am -
Nonstop1h 09m
Deal found 9/7![United Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 9/6. 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.
Fri 10/161:20 pm -
Nonstop1h 05m
Sun 10/189:30 pm -
Nonstop1h 00m
Deal found 9/6![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 9/7. 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 10/57:10 am -
Nonstop1h 19m
Mon 10/125:59 am -
Nonstop1h 12m
Deal found 9/7![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 9/5. 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.
Wed 10/73:47 pm -
1 stop5h 43m
Sun 10/187:30 pm -
1 stop3h 26m
Deal found 9/5![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 9/5. 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.
Fri 10/25:35 pm -
Nonstop1h 05m
Sat 10/36:45 am -
1 stop6h 25m
Deal found 9/5![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 9/5. 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.
Thu 10/16:45 am -
Nonstop1h 00m
Sat 10/36:45 am -
1 stop6h 25m
Deal found 9/5![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 9/6. 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.
Fri 10/162:09 pm -
1 stop3h 23m
Sun 10/187:30 pm -
1 stop3h 26m
Deal found 9/6![Delta logo]()
$367
Last-minute flights from Grand Rapids to ChicagoDiscover last-minute flight deals from Grand Rapids to Chicago. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Grand Rapids to Chicago. Data last updated September 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 10/11:20 pm -
Nonstop1h 05m
Sat 10/310:25 am -
Nonstop0h 55m
Deal found 9/9![Southwest logo]()
$265
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:50 am -
Nonstop1h 18m
Sat 10/311:00 am -
Nonstop1h 09m
Deal found 9/9![United Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 9/8. 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 10/15:30 am -
1 stop4h 37m
Sat 10/39:29 am -
1 stop4h 29m
Deal found 9/8![Delta logo]()
$285
This Delta deal was found by Cheapflights users on 9/8. 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 10/15:30 am -
1 stop3h 26m
Sat 10/38:55 am -
1 stop5h 03m
Deal found 9/8![Delta logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/14:24 pm -
1 stop8h 59m
Sat 10/36:30 am -
1 stop7h 56m
Deal found 9/9![Frontier logo]()
$301
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Sat 10/109:38 am -
Nonstop1h 30m
Mon 10/126:45 am -
Nonstop1h 18m
Deal found 9/7![American Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 9/7. 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 10/121:20 pm -
Nonstop1h 05m
Fri 10/239:40 am -
Nonstop0h 55m
Deal found 9/7![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 9/8. 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 10/145:35 am -
1 stop6h 45m
Fri 10/305:00 am -
1 stop6h 40m
Deal found 9/8![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 9/6. 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.
Thu 10/151:20 pm -
Nonstop1h 05m
Mon 10/199:45 pm -
Nonstop1h 00m
Deal found 9/6![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:15 pm -
Nonstop1h 20m
Mon 10/269:50 pm -
Nonstop1h 08m
Deal found 9/9![United Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Fri 10/235:17 pm -
1 stop6h 22m
Wed 10/287:28 pm -
2 stops43h 59m
Deal found 9/8![Multiple Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 9/8. 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.
Fri 10/232:09 pm -
1 stop5h 20m
Wed 10/285:29 pm -
1 stop5h 27m
Deal found 9/8![Delta logo]()
$298
One-way flights from Grand Rapids to ChicagoSearch for one-way flight options from Grand Rapids to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Grand Rapids to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:01 pm -
1 stop9h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:00 am -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 9/8. 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 10/76:50 am -
Nonstop1h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$133
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/410:19 am -
Nonstop1h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$133
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:30 am -
1 stop5h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$143
This Delta deal was found by Cheapflights users on 9/8. 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 11/55:30 am -
1 stop3h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$143
This Southwest deal was found by Cheapflights users on 9/9. 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.
Fri 10/21:20 pm -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$146
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:01 am -
Nonstop1h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![United Airlines logo]()
$146
This Southwest deal was found by Cheapflights users on 9/5. 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.
Mon 10/55:35 pm -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Southwest logo]()
$147
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 10/213:57 pm -
Nonstop1h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:00 am -
2 stops16h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:03 pm -
2 stops29h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$152
Find 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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $265 (Southwest) |
One-way from | $120 (Kiwi.com) |
Popular in | January |
Cheapest in | March |
Average price | $265 |
Good round-trip deal | $380 or less |
Good one-way deal | $191 or less |
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 7,457,451 searches. Data last updated September 10, 2026.
Use the filters below to find and compare flights from Grand Rapids to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Thu 10/8
5:35 pm-5:40 pm
Nonstop1h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Sat 11/7
3:47 pm-6:00 pm
1 stop3h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Wed 10/7
3:47 pm-8:30 pm
1 stop5h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Fri 11/6
6:30 am-6:35 am
Nonstop1h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$155
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Fri 10/2
2:45 pm-5:55 pm
1 stop4h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Wed 1/6
8:15 am-12:33 pm
1 stop5h 18m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Thu 11/5
5:30 am-9:32 am
1 stop5h 02m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Mon 12/14
2:12 pm-6:01 pm
1 stop4h 49m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Mon 11/2
2:09 pm-6:00 pm
1 stop4h 51m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Sat 1/9
8:15 am-12:33 pm
1 stop5h 18m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
Showing 1-10 of 42 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
GRR-CHI
GRR-MDW
GRR-ORD
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
GRR-CHI
GRR-MDW
GRR-ORD
What is the cheapest month to book a flight from Grand Rapids to Chicago?
Currently, November is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $171). Flying from Grand Rapids to Chicago in August is currently the most expensive (average of $536). 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 10, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Grand Rapids to Chicago by exploring options for tickets in the morning.
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 10, 2026.
The most flights from GRR to CHI are scheduled on a Tuesday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
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 5, 2026.
Travelers seeking maximum savings on their Grand Rapids to Chicago flight should consider departing on Monday at noon 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.
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 10, 2026.
See what other customers who have flown with 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.
Comfort
7.3
Food
6.6
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.6
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.6
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
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Grand Rapids and Chicago flights
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Other flights from Grand Rapids
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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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$201 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$296 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$289 | FlexibilityNo cancel fee | On-time71% |