$129+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
Dec 5 — Dec 121
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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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 November 5, 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 November 5, 2026.
This Southwest deal was found by Cheapflights users on 11/3. 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 12/17:20 pm -
Nonstop1h 20m
Tue 12/86:15 pm -
Nonstop1h 05m
Deal found 11/3![Southwest logo]()
$257
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/142:31 pm -
Nonstop1h 26m
Wed 12/1611:45 am -
Nonstop1h 16m
Deal found 11/3![American Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 11/2. 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 12/512:55 pm -
1 stop7h 45m
Mon 12/78:25 am -
Nonstop1h 00m
Deal found 11/2![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 11/2. 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 12/152:12 pm -
1 stop4h 49m
Thu 12/179:37 am -
1 stop2h 55m
Deal found 11/2![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 11/3. 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 12/145:44 pm -
1 stop3h 31m
Wed 12/165:02 pm -
1 stop6h 02m
Deal found 11/3![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 11/1. 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 12/47:05 am -
Nonstop1h 10m
Sun 12/62:50 pm -
Nonstop0h 55m
Deal found 11/1![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/48:45 am -
Nonstop1h 25m
Sun 12/69:51 pm -
Nonstop1h 08m
Deal found 11/1![United Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/223:30 pm -
Nonstop1h 29m
Sat 12/269:43 pm -
Nonstop1h 16m
Deal found 11/4![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:20 pm -
Nonstop1h 25m
Sun 12/136:10 pm -
1 stop5h 15m
Deal found 11/4![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 10/31. 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 12/205:20 am -
2 stops9h 25m
Mon 12/219:30 pm -
Nonstop1h 05m
Deal found 10/31![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 11/4. 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 12/175:30 am -
1 stop5h 07m
Sat 12/196:15 pm -
1 stop4h 37m
Deal found 11/4![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 11/1. 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
Fri 11/277:05 am -
1 stop5h 42m
Deal found 11/1![Delta logo]()
$308
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 November 5, 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 November 5, 2026.
This Southwest deal was found by Cheapflights users on 11/3. 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 1/1112:25 pm -
Nonstop1h 10m
Thu 1/148:20 am -
Nonstop1h 05m
Deal found 11/3![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 10/31. 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 12/145:44 pm -
1 stop3h 31m
Tue 12/158:39 am -
1 stop5h 30m
Deal found 10/31![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Sun 12/206:25 pm -
Nonstop1h 40m
Mon 12/219:43 pm -
Nonstop1h 16m
Deal found 10/31![United Airlines logo]()
$292
This KAYAK deal was found by Cheapflights users on 11/4. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:48 am -
Nonstop1h 42m
Thu 11/191:27 pm -
Nonstop1h 08m
Deal found 11/4![American Airlines logo]()
$463
This Southwest deal was found by Cheapflights users on 10/31. 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 1/294:05 pm -
Nonstop1h 15m
Sat 2/610:05 am -
Nonstop1h 00m
Deal found 10/31![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 11/3. 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 12/33:51 pm -
1 stop3h 35m
Mon 12/75:02 pm -
1 stop6h 02m
Deal found 11/3![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 11/2. 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 12/51:55 pm -
Nonstop1h 15m
Mon 12/71:15 pm -
2 stops8h 15m
Deal found 11/2![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 10/31. 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 10/31![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/55:25 am -
2 stops8h 35m
Fri 2/121:30 pm -
Nonstop0h 55m
Deal found 11/4![Southwest logo]()
$272
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/44:49 pm -
Nonstop1h 26m
Mon 12/74:20 pm -
Nonstop1h 14m
Deal found 11/3![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 10/31. 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 12/65:44 pm -
1 stop3h 31m
Thu 12/108:39 am -
1 stop5h 30m
Deal found 10/31![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 10/31. 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 12/205:45 pm -
Nonstop1h 15m
Mon 12/219:30 pm -
Nonstop1h 05m
Deal found 10/31![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 11/1. 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 4/289:25 am -
Nonstop1h 18m
Sun 5/29:50 pm -
Nonstop1h 03m
Deal found 11/1![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 11/1. 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 12/212:13 pm -
1 stop4h 31m
Mon 12/286:15 pm -
1 stop4h 37m
Deal found 11/1![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 11/1. 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 12/215:20 am -
1 stop7h 55m
Mon 12/289:30 pm -
Nonstop1h 05m
Deal found 11/1![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 11/3. 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
Sat 11/2811:19 am -
1 stop4h 51m
Deal found 11/3![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:20 am -
Nonstop1h 10m
Sun 12/274:30 pm -
Nonstop1h 00m
Deal found 11/4![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 11/1. 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 12/236:50 am -
1 stop3h 59m
Sun 12/277:00 am -
1 stop5h 32m
Deal found 11/1![Delta logo]()
$411
This Southwest deal was found by Cheapflights users on 11/3. 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 4/166:40 am -
Nonstop1h 10m
Sun 4/189:50 am -
Nonstop0h 55m
Deal found 11/3![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/265:50 pm -
Nonstop1h 10m
Sat 12/2610:25 pm -
Nonstop1h 05m
Deal found 11/4![Southwest logo]()
$403
Last-minute flights from Grand Rapids to ChicagoDiscover last-minute flight deals from Grand Rapids to Chicago. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Grand Rapids to Chicago. Data last updated November 5, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 11/1. 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
Fri 11/277:05 am -
1 stop5h 42m
Deal found 11/1![Delta logo]()
$308
This Southwest deal was found by Cheapflights users on 11/3. 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 12/17:20 pm -
Nonstop1h 20m
Tue 12/86:15 pm -
Nonstop1h 05m
Deal found 11/3![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 11/1. 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 12/47:05 am -
Nonstop1h 10m
Sun 12/62:50 pm -
Nonstop0h 55m
Deal found 11/1![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/48:45 am -
Nonstop1h 25m
Sun 12/69:51 pm -
Nonstop1h 08m
Deal found 11/1![United Airlines logo]()
$292
This Southwest deal was found by Cheapflights users on 11/2. 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 12/512:55 pm -
1 stop7h 45m
Mon 12/78:25 am -
Nonstop1h 00m
Deal found 11/2![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:20 pm -
Nonstop1h 25m
Sun 12/136:10 pm -
1 stop5h 15m
Deal found 11/4![Southwest logo]()
$302
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/142:31 pm -
Nonstop1h 26m
Wed 12/1611:45 am -
Nonstop1h 16m
Deal found 11/3![American Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 11/3. 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 12/145:44 pm -
1 stop3h 31m
Wed 12/165:02 pm -
1 stop6h 02m
Deal found 11/3![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 11/2. 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 12/155:30 am -
1 stop5h 07m
Wed 12/169:37 am -
1 stop2h 55m
Deal found 11/2![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 11/4. 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 12/175:30 am -
1 stop5h 07m
Sat 12/196:15 pm -
1 stop4h 37m
Deal found 11/4![Delta logo]()
$308
This Southwest deal was found by Cheapflights users on 10/31. 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 12/205:20 am -
2 stops9h 25m
Mon 12/219:30 pm -
Nonstop1h 05m
Deal found 10/31![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/223:30 pm -
Nonstop1h 29m
Sat 12/269:43 pm -
Nonstop1h 16m
Deal found 11/4![United Airlines logo]()
$295
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 November 5, 2026.
Search for one-way flight options from Grand Rapids to Chicago. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Southwest deal was found by Cheapflights users on 10/31. 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 11/271:25 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Southwest logo]()
$129
This American Airlines deal was found by Cheapflights users on 11/1. 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 2/45:34 am -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$129
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/154:28 pm -
Nonstop1h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$134
This Delta deal was found by Cheapflights users on 11/3. 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 2/43:46 pm -
1 stop3h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$139
This Delta deal was found by Cheapflights users on 11/3. 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 2/42:07 pm -
1 stop3h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/712:05 pm -
2 stops34h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$145
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Sun 12/206:25 pm -
Nonstop1h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![United Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 11/2. 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 4/195:40 pm -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$167
This United Airlines deal was found by Cheapflights users on 11/3. 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 3/246:43 am -
Nonstop1h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/204:53 pm -
2 stops33h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/712:30 pm -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:41 pm -
Nonstop1h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![United Airlines logo]()
$174
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Southwest) |
One-way from | $129 (Southwest) |
Popular in | January |
Cheapest in | March |
Average price | $532 |
Good round-trip deal | $375 or less |
Good one-way deal | $229 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 November 5, 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
Fri 11/27
1:25 pm-1:45 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Fri 11/27
12:00 pm-12:27 pm
Nonstop1h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Wed 12/2
11:00 am-11:15 am
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Thu 12/3
8:05 pm-8:31 pm
Nonstop1h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Wed 12/2
5:30 am-9:37 am
1 stop5h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Thu 2/4
3:46 pm-6:00 pm
1 stop3h 14m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway
GRRMDW
Grand Rapids Gerald R. Ford Intl
Fri 11/27
6:55 am-11:25 am
1 stop5h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Wed 12/30
6:50 am-9:49 am
1 stop3h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Sat 1/30
7:25 am-9:53 am
1 stop3h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Grand RapidsChicago
GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl
GRRORD
Grand Rapids Gerald R. Ford Intl
Wed 12/2
5:30 am-10:59 am
1 stop6h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Showing 1-10 of 40 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 November 5, 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 November 5, 2026.
The most flights from GRR to CHI are scheduled on a Monday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 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 October 31, 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 November 5, 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.
Entertainment
7.1
Comfort
7.3
Overall
7.3
Boarding
7.7
Crew
8.1
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Comfort
7.3
Overall
7.3
Boarding
7.7
Crew
8.1
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Comfort
7.3
Overall
7.3
Boarding
7.7
Crew
8.1
Food
6.7
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
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Hammond
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Other flights to Chicago
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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 November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$229 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$164 | Average$289 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$171 | Average$364 | FlexibilityNo cancel fee | On-time69% |