$106+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
Nov 22 — Nov 291
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
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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 October 23, 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 October 23, 2026.
This Southwest deal was found by Cheapflights users on 10/21. 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 11/121:25 pm -
Nonstop1h 20m
Thu 11/198:25 am -
Nonstop1h 00m
Deal found 10/21![Southwest logo]()
$211
This United Airlines deal was found by Cheapflights users on 10/19. 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 12/148:05 pm -
Nonstop1h 26m
Tue 12/159:00 am -
Nonstop1h 20m
Deal found 10/19![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 10/19. 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 11/1911:00 am -
Nonstop1h 15m
Mon 11/239:20 pm -
Nonstop1h 10m
Deal found 10/19![Southwest logo]()
$212
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/125:50 am -
Nonstop1h 19m
Thu 11/191:27 pm -
Nonstop1h 08m
Deal found 10/21![American Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 10/23. 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 12/131:25 pm -
Nonstop1h 20m
Thu 12/179:20 pm -
Nonstop1h 10m
Deal found 10/23![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 10/22. 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 12/147:05 am -
Nonstop1h 10m
Wed 12/161:15 pm -
2 stops8h 15m
Deal found 10/22![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 10/20. 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 11/233:41 pm -
1 stop3h 23m
Thu 11/2612:05 pm -
1 stop5h 58m
Deal found 10/20![Delta logo]()
$231
This Delta deal was found by Cheapflights users on 10/19. 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 35m
Tue 12/1511:39 am -
1 stop4h 25m
Deal found 10/19![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/23. 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 11/187:20 pm -
Nonstop1h 20m
Fri 11/209:20 pm -
Nonstop1h 10m
Deal found 10/23![Southwest logo]()
$241
This United Airlines deal was found by Cheapflights users on 10/22. 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 12/188:45 am -
Nonstop1h 32m
Mon 1/113:38 pm -
Nonstop1h 22m
Deal found 10/22![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 10/22. 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 11/125:30 am -
1 stop9h 10m
Thu 11/129:20 pm -
Nonstop1h 10m
Deal found 10/22![Southwest logo]()
$251
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/129:16 pm -
Nonstop1h 29m
Sun 11/1510:35 pm -
Nonstop1h 06m
Deal found 10/21![American Airlines logo]()
$256
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 October 23, 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 October 23, 2026.
This Southwest deal was found by Cheapflights users on 10/22. 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 11/121:25 pm -
Nonstop1h 20m
Thu 11/129:20 pm -
Nonstop1h 10m
Deal found 10/22![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 10/20. 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 11/233:41 pm -
1 stop3h 23m
Thu 11/2612:05 pm -
1 stop5h 58m
Deal found 10/20![Delta logo]()
$231
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/253:34 pm -
Nonstop1h 24m
Sun 11/299:50 pm -
Nonstop1h 08m
Deal found 10/20![United Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 10/19. 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 11/1911:00 am -
Nonstop1h 15m
Mon 11/239:20 pm -
Nonstop1h 10m
Deal found 10/19![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 10/22. 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 11/253:41 pm -
1 stop5h 36m
Tue 12/88:39 am -
1 stop5h 30m
Deal found 10/22![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/22. 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 11/125:30 am -
1 stop9h 10m
Mon 11/168:25 am -
Nonstop1h 00m
Deal found 10/22![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 10/18. 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 1/1512:30 pm -
Nonstop1h 27m
Tue 1/191:55 pm -
Nonstop1h 20m
Deal found 10/18![United Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 10/22. 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 11/125:30 am -
1 stop5h 16m
Mon 11/166:44 pm -
1 stop4h 14m
Deal found 10/22![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 10/20. 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 11/1911:00 am -
Nonstop1h 15m
Sun 11/222:50 pm -
Nonstop0h 55m
Deal found 10/20![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 10/19. 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 12/115:30 am -
1 stop5h 07m
Sun 12/136:41 pm -
1 stop4h 23m
Deal found 10/19![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 10/21. 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 2/75:25 am -
1 stop9h 05m
Wed 2/178:20 am -
Nonstop1h 05m
Deal found 10/21![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 10/23. 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.
Sun 12/1310:42 am -
1 stop4h 14m
Thu 12/177:15 pm -
1 stop3h 49m
Deal found 10/23![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 10/23. 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 11/187:05 am -
Nonstop1h 10m
Fri 11/206:10 pm -
1 stop5h 15m
Deal found 10/23![Southwest logo]()
$321
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/125:45 am -
2 stops12h 06m
Thu 11/127:57 pm -
Nonstop1h 07m
Deal found 10/22![United Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 10/19. 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 12/75:44 pm -
1 stop3h 31m
Thu 12/107:15 pm -
1 stop3h 49m
Deal found 10/19![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 10/18. 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 11/213:41 pm -
1 stop5h 36m
Mon 11/232:44 pm -
1 stop5h 15m
Deal found 10/18![Delta logo]()
$353
This Southwest deal was found by Cheapflights users on 10/22. 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 11/61:25 pm -
Nonstop1h 20m
Tue 11/108:25 am -
Nonstop1h 00m
Deal found 10/22![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 10/22. 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 12/148:05 pm -
Nonstop1h 26m
Wed 12/167:00 am -
1 stop14h 25m
Deal found 10/22![United Airlines logo]()
$486
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/218:00 am -
1 stop16h 59m
Mon 11/231:55 pm -
Nonstop1h 11m
Deal found 10/21![United Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 10/18. 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 12/285:45 pm -
Nonstop1h 15m
Tue 12/294:05 pm -
1 stop7h 25m
Deal found 10/18![Southwest logo]()
$373
This Delta deal was found by Cheapflights users on 10/22. 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 11/133:41 pm -
1 stop3h 49m
Sun 11/158:29 am -
1 stop5h 32m
Deal found 10/22![Delta logo]()
$385
This Delta deal was found by Cheapflights users on 10/20. 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 12/115:44 pm -
1 stop3h 31m
Sat 12/122:41 pm -
1 stop5h 30m
Deal found 10/20![Delta logo]()
$428
This Delta deal was found by Cheapflights users on 10/19. 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.
Sun 11/222:27 pm -
1 stop2h 51m
Sat 11/287:25 am -
1 stop5h 22m
Deal found 10/19![Delta logo]()
$429
Last-minute flights from Grand Rapids to ChicagoDiscover last-minute flight deals from Grand Rapids to Chicago. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Grand Rapids to Chicago. Data last updated October 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/21. 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 11/121:25 pm -
Nonstop1h 20m
Thu 11/198:25 am -
Nonstop1h 00m
Deal found 10/21![Southwest logo]()
$211
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/125:50 am -
Nonstop1h 19m
Thu 11/191:27 pm -
Nonstop1h 08m
Deal found 10/21![American Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 10/22. 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 11/125:30 am -
1 stop9h 10m
Thu 11/129:20 pm -
Nonstop1h 10m
Deal found 10/22![Southwest logo]()
$251
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/129:16 pm -
Nonstop1h 29m
Sun 11/1510:35 pm -
Nonstop1h 06m
Deal found 10/21![American Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:14 pm -
Nonstop1h 25m
Sun 11/156:30 pm -
Nonstop1h 16m
Deal found 10/22![American Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 10/23. 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 11/187:20 pm -
Nonstop1h 20m
Fri 11/209:20 pm -
Nonstop1h 10m
Deal found 10/23![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 10/19. 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 11/1911:00 am -
Nonstop1h 15m
Mon 11/239:20 pm -
Nonstop1h 10m
Deal found 10/19![Southwest logo]()
$212
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/219:31 pm -
Nonstop1h 42m
Mon 11/236:45 pm -
Nonstop1h 16m
Deal found 10/21![American Airlines logo]()
$211
This Delta deal was found by Cheapflights users on 10/19. 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 11/213:41 pm -
1 stop5h 36m
Mon 11/232:44 pm -
1 stop5h 15m
Deal found 10/19![Delta logo]()
$231
This Delta deal was found by Cheapflights users on 10/20. 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 11/233:41 pm -
1 stop3h 23m
Thu 11/2612:05 pm -
1 stop5h 58m
Deal found 10/20![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/20. 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 11/235:30 am -
1 stop9h 10m
Thu 11/269:25 am -
Nonstop0h 55m
Deal found 10/20![Southwest logo]()
$288
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/259:31 pm -
Nonstop1h 42m
Sat 11/2810:35 pm -
Nonstop1h 04m
Deal found 10/21![American Airlines logo]()
$272
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 October 23, 2026.
Search for one-way flight options from Grand Rapids to Chicago. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Southwest deal was found by Cheapflights users on 10/21. 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 11/146:35 am -
Nonstop1h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$106
This American Airlines deal was found by Cheapflights users on 10/21. 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 2/42:18 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$106
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/302:41 pm -
Nonstop1h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$110
This Delta deal was found by Cheapflights users on 10/21. 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 11/185:30 am -
1 stop6h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$116
This Southwest deal was found by Cheapflights users on 10/21. 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 11/131:25 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$119
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/138:40 am -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 10/21. 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 11/133:41 pm -
1 stop3h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$146
This Delta deal was found by Cheapflights users on 10/20. 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 12/296:00 pm -
1 stop3h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$146
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/125:32 am -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Sun 12/133:31 pm -
2 stops21h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$163
This Southwest deal was found by Cheapflights users on 10/21. 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 12/295:45 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$167
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/287:00 am -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$167
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 October 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $211 (Southwest) |
One-way from | $106 (Southwest) |
Popular in | January |
Cheapest in | March |
Average price | $327 |
Good round-trip deal | $369 or less |
Good one-way deal | $223 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 October 23, 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
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Sat 11/14
6:35 am-6:45 am
Nonstop1h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Wed 11/18
5:30 am-10:39 am
1 stop6h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$116
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Fri 11/13
3:41 pm-6:04 pm
1 stop3h 23m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Fri 11/13
5:50 pm-8:17 pm
1 stop3h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Tue 12/29
5:45 pm-6:00 pm
Nonstop1h 15m
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 12/3
7:40 am-9:37 am
1 stop2h 57m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$177
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Wed 12/30
6:00 pm-8:18 pm
1 stop3h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$177
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Sun 12/13
10:42 am-1:01 pm
1 stop3h 19m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Sun 12/13
3:51 pm-8:15 pm
1 stop5h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Thu 11/19
5:30 am-7:49 am
1 stop3h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$186
Showing 1-10 of 45 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 October.
| 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, March is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $217). 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 October 23, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 15% 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 October 23, 2026.
The most flights from GRR to CHI are scheduled on a Thursday (54 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 on average).
How much does it cost to fly round-trip from Grand Rapids to Chicago?
Airfare is below average for this route at the moment.
Grand Rapids to Chicago flights typically cost between $244 and $320 in November.The cheapest round-trip price found within the last 5 days was $211 on Southwest (Nov 12-Nov 19).
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 17, 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. Friday 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 October 23, 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.
Overall
7.3
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
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
Merrillville
Lansing
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Hammond
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Porter
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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 October 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$229 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$349 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$164 | Average$289 | FlexibilityNo cancel fee | On-time71% |