$49+ Cheap flights from Grand Rapids (GRR) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
Apr 6 — Apr 131
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 March 7, 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 March 7, 2026.
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Tue 3/247:42 pm
GRR
- ORD
Nonstop1h 14m
American Airlines
Wed 3/254:55 pm
ORD
- GRR
Nonstop0h 59m
American Airlines
Deal found 3/3![American Airlines logo]()
$117
This United Airlines deal was found by Cheapflights users on 3/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:40 pm
GRR
- ORD
Nonstop1h 12m
United Airlines
Mon 4/2710:45 am
ORD
- GRR
Nonstop1h 06m
United Airlines
Deal found 3/5![United Airlines logo]()
$134
This American Airlines deal was found by Cheapflights users on 3/2. 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 4/74:17 pm
GRR
- ORD
Nonstop1h 19m
American Airlines
Thu 4/97:14 am
ORD
- GRR
Nonstop1h 10m
American Airlines
Deal found 3/2![American Airlines logo]()
$154
This Delta deal was found by Cheapflights users on 3/4. 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.
Tue 3/315:30 am
GRR
- MDW
1 stop4h 23m
Delta
Tue 4/76:34 pm
MDW
- GRR
1 stop4h 08m
Delta
Deal found 3/4![Delta logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Sat 4/185:34 am
GRR
- ORD
Nonstop1h 16m
American Airlines
Mon 4/2010:10 pm
ORD
- GRR
Nonstop1h 07m
American Airlines
Deal found 3/2![American Airlines logo]()
$171
This Delta deal was found by Cheapflights users on 3/3. 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.
Tue 3/245:30 am
GRR
- ORD
1 stop4h 40m
Delta
Wed 3/259:50 am
ORD
- GRR
1 stop2h 51m
Delta
Deal found 3/3![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:38 pm
GRR
- ORD
Nonstop1h 12m
United Airlines
Tue 4/289:50 pm
ORD
- GRR
Nonstop1h 09m
United Airlines
Deal found 3/2![United Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 3/3. 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.
Sat 4/185:05 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Sat 4/186:15 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 3/3![Southwest logo]()
$181
This Delta deal was found by Cheapflights users on 3/5. 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.
Sat 4/185:29 am
GRR
- MDW
1 stop4h 18m
Delta
Mon 4/209:27 am
MDW
- GRR
1 stop4h 42m
Delta
Deal found 3/5![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 3/5. 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.
Sat 4/185:29 am
GRR
- ORD
1 stop5h 50m
Delta
Mon 4/208:52 am
ORD
- GRR
1 stop5h 17m
Delta
Deal found 3/5![Delta logo]()
$191
This American Airlines deal was found by Cheapflights users on 3/4. 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.
Mon 4/67:42 pm
GRR
- ORD
Nonstop1h 14m
American Airlines
Thu 4/97:14 am
ORD
- GRR
Nonstop1h 10m
American Airlines
Deal found 3/4![American Airlines logo]()
$223
This United Airlines deal was found by Cheapflights users on 3/3. 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.
Sat 3/289:20 am
GRR
- ORD
Nonstop1h 12m
United Airlines
Mon 3/3012:52 pm
ORD
- GRR
Nonstop1h 06m
United Airlines
Deal found 3/3![United Airlines logo]()
$230
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 March 7, 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 March 7, 2026.
This United Airlines deal was found by Cheapflights users on 3/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:40 pm
GRR
- ORD
Nonstop1h 12m
United Airlines
Mon 4/2710:45 am
ORD
- GRR
Nonstop1h 06m
United Airlines
Deal found 3/5![United Airlines logo]()
$134
This Delta deal was found by Cheapflights users on 3/2. 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 3/243:34 pm
GRR
- ORD
1 stop4h 00m
Delta
Wed 3/259:50 am
ORD
- GRR
1 stop2h 51m
Delta
Deal found 3/2![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 3/3. 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.
Sat 4/185:30 am
GRR
- MDW
1 stop8h 40m
Southwest
Sat 4/185:25 pm
MDW
- GRR
1 stop5h 00m
Southwest
Deal found 3/3![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 3/5. 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.
Tue 6/25:05 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Thu 6/111:15 pm
MDW
- GRR
Nonstop0h 50m
Southwest
Deal found 3/5![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Sat 3/214:55 pm
GRR
- ORD
Nonstop1h 08m
United Airlines
Mon 3/237:53 pm
ORD
- GRR
Nonstop1h 06m
United Airlines
Deal found 3/1![United Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 3/2. 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 3/315:30 am
GRR
- MDW
1 stop4h 23m
Delta
Tue 4/76:34 pm
MDW
- GRR
1 stop4h 08m
Delta
Deal found 3/2![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 3/2. 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.
Sat 4/185:29 am
GRR
- MDW
1 stop4h 18m
Delta
Mon 4/209:27 am
MDW
- GRR
1 stop4h 42m
Delta
Deal found 3/2![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 3/2. 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 3/215:50 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Mon 3/239:40 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 3/2![Southwest logo]()
$296
This United Airlines deal was found by Cheapflights users on 3/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/257:25 am
GRR
- ORD
Nonstop1h 12m
United Airlines
Thu 3/2610:45 am
ORD
- GRR
Nonstop1h 10m
United Airlines
Deal found 3/5![United Airlines logo]()
$306
This KAYAK deal was found by Cheapflights users on 3/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/133:50 pm
GRR
- ORD
1 stop4h 02m
Delta
Fri 4/175:04 pm
ORD
- GRR
1 stop2h 53m
Delta
Deal found 3/6![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 3/4. 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.
Fri 5/152:21 pm
GRR
- ORD
1 stop4h 44m
Delta
Thu 5/217:00 am
ORD
- GRR
1 stop3h 18m
Delta
Deal found 3/4![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 3/6. 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 4/246:10 pm
GRR
- ORD
1 stop3h 30m
Delta
Sun 4/267:43 pm
ORD
- GRR
1 stop3h 14m
Delta
Deal found 3/6![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 3/4. 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 4/13:10 pm
GRR
- MDW
1 stop5h 25m
Southwest
Wed 4/89:40 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 3/4![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 3/3. 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.
Fri 4/176:10 pm
GRR
- ORD
1 stop3h 30m
Delta
Sun 4/197:43 pm
ORD
- GRR
1 stop3h 14m
Delta
Deal found 3/3![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 3/4. 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.
Fri 4/175:29 am
GRR
- MDW
1 stop4h 18m
Delta
Sun 4/196:38 pm
MDW
- GRR
1 stop4h 19m
Delta
Deal found 3/4![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 3/3. 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.
Fri 3/272:21 pm
GRR
- MDW
1 stop4h 33m
Delta
Sat 3/281:10 pm
MDW
- GRR
1 stop3h 32m
Delta
Deal found 3/3![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 3/3. 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.
Sat 3/2810:49 am
GRR
- ORD
1 stop3h 35m
Delta
Mon 3/305:40 pm
ORD
- GRR
1 stop5h 02m
Delta
Deal found 3/3![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 3/6. 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.
Sun 3/228:10 am
GRR
- MDW
1 stop5h 19m
Delta
Tue 3/249:35 am
MDW
- GRR
1 stop4h 19m
Delta
Deal found 3/6![Delta logo]()
$443
Last-minute flights from Grand Rapids to ChicagoDiscover last-minute flight deals from Grand Rapids to Chicago. Data last updated March 7, 2026 and is based on user searches.
Discover last-minute flight deals from Grand Rapids to Chicago. Data last updated March 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Tue 3/247:42 pm
GRR
- ORD
Nonstop1h 14m
American Airlines
Wed 3/254:55 pm
ORD
- GRR
Nonstop0h 59m
American Airlines
Deal found 3/3![American Airlines logo]()
$117
This Delta deal was found by Cheapflights users on 3/3. 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.
Tue 3/245:30 am
GRR
- ORD
1 stop4h 40m
Delta
Wed 3/259:50 am
ORD
- GRR
1 stop2h 51m
Delta
Deal found 3/3![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 3/3. 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.
Sat 3/289:20 am
GRR
- ORD
Nonstop1h 12m
United Airlines
Mon 3/3012:52 pm
ORD
- GRR
Nonstop1h 06m
United Airlines
Deal found 3/3![United Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 3/4. 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.
Tue 3/315:30 am
GRR
- MDW
1 stop4h 23m
Delta
Tue 4/76:34 pm
MDW
- GRR
1 stop4h 08m
Delta
Deal found 3/4![Delta logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/4. 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.
Mon 4/67:42 pm
GRR
- ORD
Nonstop1h 14m
American Airlines
Thu 4/97:14 am
ORD
- GRR
Nonstop1h 10m
American Airlines
Deal found 3/4![American Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 3/2. 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 4/74:17 pm
GRR
- ORD
Nonstop1h 19m
American Airlines
Thu 4/97:14 am
ORD
- GRR
Nonstop1h 10m
American Airlines
Deal found 3/2![American Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Sat 4/185:34 am
GRR
- ORD
Nonstop1h 16m
American Airlines
Mon 4/2010:10 pm
ORD
- GRR
Nonstop1h 07m
American Airlines
Deal found 3/2![American Airlines logo]()
$171
This Southwest deal was found by Cheapflights users on 3/3. 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.
Sat 4/185:05 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Sat 4/186:15 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 3/3![Southwest logo]()
$181
This Delta deal was found by Cheapflights users on 3/5. 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.
Sat 4/185:29 am
GRR
- MDW
1 stop4h 18m
Delta
Mon 4/209:27 am
MDW
- GRR
1 stop4h 42m
Delta
Deal found 3/5![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 3/5. 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.
Sat 4/185:29 am
GRR
- ORD
1 stop5h 50m
Delta
Mon 4/208:52 am
ORD
- GRR
1 stop5h 17m
Delta
Deal found 3/5![Delta logo]()
$191
This United Airlines deal was found by Cheapflights users on 3/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:40 pm
GRR
- ORD
Nonstop1h 12m
United Airlines
Mon 4/2710:45 am
ORD
- GRR
Nonstop1h 06m
United Airlines
Deal found 3/5![United Airlines logo]()
$134
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:38 pm
GRR
- ORD
Nonstop1h 12m
United Airlines
Tue 4/289:50 pm
ORD
- GRR
Nonstop1h 09m
United Airlines
Deal found 3/2![United Airlines logo]()
$178
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 March 7, 2026.
Search for one-way flight options from Grand Rapids to Chicago. Find affordable one-way fares based on user searches. Data last updated March 7, 2026.
This Southwest deal was found by Cheapflights users on 3/3. 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.
Wed 4/295:05 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Deal found 3/3![Southwest logo]()
$49
This United Airlines deal was found by Cheapflights users on 3/3. 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.
Tue 4/712:58 pm
GRR
- ORD
Nonstop1h 17m
United Airlines
Deal found 3/3![United Airlines logo]()
$49
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Wed 4/2910:27 am
GRR
- ORD
Nonstop1h 21m
American Airlines
Deal found 3/3![American Airlines logo]()
$59
This American Airlines deal was found by Cheapflights users on 3/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:17 pm
GRR
- ORD
Nonstop1h 19m
American Airlines
Deal found 3/6![American Airlines logo]()
$70
This American Airlines deal was found by Cheapflights users on 3/7. 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 5/165:00 am
GRR
- ORD
Nonstop1h 11m
American Airlines
Deal found 3/7![American Airlines logo]()
$72
This Delta deal was found by Cheapflights users on 3/5. 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 4/73:53 pm
GRR
- MDW
1 stop3h 47m
Delta
Deal found 3/5![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 3/4. 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.
Tue 5/512:19 pm
GRR
- ORD
1 stop4h 59m
Delta
Deal found 3/4![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 3/5. 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 4/77:19 am
GRR
- ORD
2 stops6h 58m
Delta
Deal found 3/5![Delta logo]()
$84
This Southwest deal was found by Cheapflights users on 3/2. 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 4/65:50 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Deal found 3/2![Southwest logo]()
$86
This United Airlines deal was found by Cheapflights users on 3/3. 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.
Thu 4/95:03 pm
GRR
- ORD
Nonstop1h 02m
United Airlines
Deal found 3/3![United Airlines logo]()
$86
This Delta deal was found by Cheapflights users on 3/3. 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.
Tue 3/315:30 am
GRR
- MDW
1 stop4h 23m
Delta
Deal found 3/3![Delta logo]()
$89
This Delta deal was found by Cheapflights users on 3/3. 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.
Tue 4/143:50 pm
GRR
- ORD
1 stop4h 02m
Delta
Deal found 3/3![Delta logo]()
$89
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 March 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (American Airlines) |
One-way from | $49 (Southwest) |
Popular in | January |
Cheapest in | October |
Average price | $217 |
Good round-trip deal | $378 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 2,558,603 searches. Data last updated March 7, 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 - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Tue 4/21
3:40 pm-3:52 pm
Nonstop1h 12m
Chicago O'Hare Intl
Mon 4/27
10:45 am-12:51 pm
Nonstop1h 06m
$134
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Tue 3/24
3:34 pm-6:34 pm
1 stop4h 00m
Chicago O'Hare Intl
Wed 3/25
9:50 am-1:41 pm
1 stop2h 51m
$191
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Sat 4/18
5:30 am-1:10 pm
1 stop8h 40m
Chicago Midway
Sat 4/18
5:25 pm-11:25 pm
1 stop5h 00m
$196
Quickest round-trip
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Tue 6/2
5:05 pm-5:10 pm
Nonstop1h 05m
Chicago Midway
Thu 6/11
1:15 pm-3:05 pm
Nonstop0h 50m
$251
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Sat 3/21
4:55 pm-5:03 pm
Nonstop1h 08m
Chicago O'Hare Intl
Mon 3/23
7:53 pm-9:59 pm
Nonstop1h 06m
$273
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Tue 3/31
5:30 am-8:53 am
1 stop4h 23m
Chicago Midway
Tue 4/7
6:34 pm-11:42 pm
1 stop4h 08m
$275
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Sat 4/18
5:29 am-8:47 am
1 stop4h 18m
Chicago Midway
Mon 4/20
9:27 am-3:09 pm
1 stop4h 42m
$283
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Sat 3/21
5:50 pm-5:55 pm
Nonstop1h 05m
Chicago Midway
Mon 3/23
9:40 pm-11:35 pm
Nonstop0h 55m
$296
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Wed 3/25
7:25 am-7:37 am
Nonstop1h 12m
Chicago O'Hare Intl
Thu 3/26
10:45 am-12:55 pm
Nonstop1h 10m
$306
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Mon 4/13
3:50 pm-6:52 pm
1 stop4h 02m
Chicago O'Hare Intl
Fri 4/17
5:04 pm-8:57 pm
1 stop2h 53m
$306
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 March.
| 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-ORD
GRR-MDW
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-ORD
GRR-MDW
What is the cheapest month to book a flight from Grand Rapids to Chicago?
Currently, October is the cheapest month in which you can book a flight from Grand Rapids to Chicago (average of $83). Flying from Grand Rapids to Chicago in February is currently the most expensive (average of $164). 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 March 7, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 21% on flights from Grand Rapids to Chicago by exploring options for tickets in the morning.
What is the cheapest day to fly from Grand Rapids to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Grand Rapids to Chicago. Price data was last updated on February 21, 2026.
Travelers seeking maximum savings on their Grand Rapids to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon 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 March 7, 2026.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Grand Rapids to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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 locationsLansing
Merrillville
Hammond
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Other flights to Chicago
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Grand Rapids and Chicago flights
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Popular flight searches
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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 2,558,603 searches. Data last updated March 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$245 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$251 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$97 | Average$201 | FlexibilityNo cancel fee | On-time63% |