$79+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
GRR — CHI
May 9 — May 161
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 April 9, 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 April 9, 2026.
This Southwest deal was found by Cheapflights users on 4/4. 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.
Tue 5/51:00 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Tue 5/129:40 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/4![Southwest logo]()
$157
This American Airlines deal was found by Cheapflights users on 4/4. 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.
Tue 5/511:30 am
GRR
- ORD
Nonstop1h 21m
American Airlines
Tue 5/128:41 am
ORD
- GRR
Nonstop1h 11m
American Airlines
Deal found 4/4![American Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:45 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Wed 8/196:30 am
MDW
- GRR
1 stop5h 30m
Southwest
Deal found 4/6![Southwest logo]()
$167
This KAYAK deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:40 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Tue 5/129:40 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/8![Southwest logo]()
$174
This KAYAK deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:34 am
GRR
- ORD
Nonstop1h 16m
American Airlines
Tue 5/1210:10 pm
ORD
- GRR
Nonstop1h 07m
American Airlines
Deal found 4/8![American Airlines logo]()
$174
This Delta deal was found by Cheapflights users on 4/4. 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 5/53:50 pm
GRR
- MDW
1 stop3h 08m
Delta
Tue 5/121:22 pm
MDW
- GRR
1 stop2h 42m
Delta
Deal found 4/4![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 4/6. 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.
Tue 5/195:30 am
GRR
- ORD
1 stop4h 15m
Delta
Tue 5/269:25 am
ORD
- GRR
1 stop3h 15m
Delta
Deal found 4/6![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 4/4. 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 5/25:05 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Sat 5/910:10 am
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/4![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Thu 4/304:07 pm
GRR
- ORD
Nonstop1h 19m
American Airlines
Mon 5/1110:10 pm
ORD
- GRR
Nonstop1h 07m
American Airlines
Deal found 4/7![American Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 4/5. 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 4/283:50 pm
GRR
- MDW
1 stop3h 08m
Delta
Thu 4/309:27 am
MDW
- GRR
1 stop4h 42m
Delta
Deal found 4/5![Delta logo]()
$194
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:43 am
GRR
- ORD
Nonstop1h 22m
American Airlines
Thu 5/147:15 am
ORD
- GRR
Nonstop1h 10m
American Airlines
Deal found 4/8![American Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 4/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:29 am
GRR
- ORD
1 stop3h 32m
Delta
Tue 5/127:00 pm
ORD
- GRR
1 stop3h 44m
Delta
Deal found 4/7![Delta logo]()
$197
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 April 9, 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 April 9, 2026.
This KAYAK deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:40 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Tue 5/129:40 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/8![Southwest logo]()
$174
This Delta deal was found by Cheapflights users on 4/4. 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 5/53:50 pm
GRR
- MDW
1 stop3h 08m
Delta
Tue 5/121:22 pm
MDW
- GRR
1 stop2h 42m
Delta
Deal found 4/4![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:09 pm
GRR
- ORD
Nonstop1h 25m
United Airlines
Tue 6/24:46 pm
ORD
- GRR
Nonstop1h 19m
United Airlines
Deal found 4/7![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 4/4. 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 5/198:16 am
GRR
- ORD
1 stop3h 13m
Delta
Tue 5/267:00 am
ORD
- GRR
1 stop3h 18m
Delta
Deal found 4/4![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 4/4. 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 5/53:50 pm
GRR
- ORD
1 stop4h 02m
Delta
Tue 5/127:00 pm
ORD
- GRR
1 stop3h 44m
Delta
Deal found 4/4![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 4/4. 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 5/25:05 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Sat 5/92:15 pm
MDW
- GRR
2 stops8h 10m
Southwest
Deal found 4/4![Southwest logo]()
$206
This Delta deal was found by Cheapflights users on 4/4. 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 6/168:11 am
GRR
- ORD
1 stop5h 53m
Delta
Wed 6/177:01 am
ORD
- GRR
1 stop6h 07m
Delta
Deal found 4/4![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Sat 5/27:17 am
GRR
- ORD
Nonstop1h 10m
United Airlines
Sat 5/27:45 pm
ORD
- GRR
Nonstop1h 10m
United Airlines
Deal found 4/5![United Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:25 am
GRR
- MDW
1 stop4h 40m
Southwest
Thu 5/143:10 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/6![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:16 am
GRR
- ORD
1 stop5h 45m
Delta
Thu 5/147:00 am
ORD
- GRR
1 stop5h 40m
Delta
Deal found 4/8![Delta logo]()
$211
This Delta deal was found by Cheapflights users on 4/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:50 pm
GRR
- ORD
1 stop4h 02m
Delta
Mon 5/117:00 pm
ORD
- GRR
1 stop3h 44m
Delta
Deal found 4/7![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:25 am
GRR
- MDW
2 stops5h 45m
Southwest
Fri 5/153:10 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/7![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 4/4. 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.
Sun 5/3110:35 am
GRR
- MDW
1 stop3h 07m
Delta
Mon 6/19:22 am
MDW
- GRR
1 stop3h 18m
Delta
Deal found 4/4![Delta logo]()
$273
This Southwest deal was found by Cheapflights users on 4/5. 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.
Sun 5/36:40 am
GRR
- MDW
Nonstop1h 00m
Southwest
Sun 5/1011:05 am
MDW
- GRR
1 stop5h 05m
Southwest
Deal found 4/5![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:30 am
GRR
- ORD
1 stop5h 59m
Delta
Mon 6/19:25 am
ORD
- GRR
1 stop3h 15m
Delta
Deal found 4/8![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 4/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:30 am
GRR
- ORD
1 stop3h 26m
Delta
Mon 9/211:35 pm
ORD
- GRR
1 stop4h 19m
Delta
Deal found 4/7![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 4/5. 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.
Sun 4/196:40 am
GRR
- MDW
Nonstop1h 00m
Southwest
Thu 4/2310:00 am
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/5![Southwest logo]()
$443
This Delta deal was found by Cheapflights users on 4/4. 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 8/275:30 am
GRR
- ORD
1 stop3h 26m
Delta
Sat 8/297:10 am
ORD
- GRR
1 stop5h 23m
Delta
Deal found 4/4![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:40 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Mon 4/273:10 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/7![Southwest logo]()
$443
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:30 am
GRR
- MDW
Nonstop1h 05m
Southwest
Sun 4/266:20 pm
MDW
- GRR
1 stop5h 05m
Southwest
Deal found 4/7![Southwest logo]()
$453
This Southwest deal was found by Cheapflights users on 4/4. 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.
Tue 4/211:00 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Tue 4/215:00 pm
MDW
- GRR
1 stop4h 35m
Southwest
Deal found 4/4![Southwest logo]()
$453
Last-minute flights from Grand Rapids to ChicagoDiscover last-minute flight deals from Grand Rapids to Chicago. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Grand Rapids to Chicago. Data last updated April 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/5. 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 4/283:50 pm
GRR
- MDW
1 stop3h 08m
Delta
Thu 4/309:27 am
MDW
- GRR
1 stop4h 42m
Delta
Deal found 4/5![Delta logo]()
$194
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Thu 4/304:07 pm
GRR
- ORD
Nonstop1h 19m
American Airlines
Mon 5/1110:10 pm
ORD
- GRR
Nonstop1h 07m
American Airlines
Deal found 4/7![American Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 4/4. 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 5/23:05 pm
GRR
- MDW
1 stop6h 35m
Southwest
Sat 5/96:15 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/4![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 4/4. 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.
Tue 5/51:00 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Tue 5/129:40 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/4![Southwest logo]()
$157
This American Airlines deal was found by Cheapflights users on 4/4. 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.
Tue 5/511:30 am
GRR
- ORD
Nonstop1h 21m
American Airlines
Tue 5/128:41 am
ORD
- GRR
Nonstop1h 11m
American Airlines
Deal found 4/4![American Airlines logo]()
$157
This Delta deal was found by Cheapflights users on 4/4. 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 5/53:50 pm
GRR
- MDW
1 stop3h 08m
Delta
Tue 5/121:22 pm
MDW
- GRR
1 stop2h 42m
Delta
Deal found 4/4![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 4/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:29 am
GRR
- ORD
1 stop3h 32m
Delta
Tue 5/127:00 pm
ORD
- GRR
1 stop3h 44m
Delta
Deal found 4/7![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:30 pm
GRR
- MDW
Nonstop1h 00m
Southwest
Thu 5/149:50 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/6![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:43 am
GRR
- ORD
Nonstop1h 22m
American Airlines
Thu 5/147:15 am
ORD
- GRR
Nonstop1h 10m
American Airlines
Deal found 4/8![American Airlines logo]()
$195
This KAYAK deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:40 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Tue 5/129:40 pm
MDW
- GRR
Nonstop0h 55m
Southwest
Deal found 4/8![Southwest logo]()
$174
This KAYAK deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:34 am
GRR
- ORD
Nonstop1h 16m
American Airlines
Tue 5/1210:10 pm
ORD
- GRR
Nonstop1h 07m
American Airlines
Deal found 4/8![American Airlines logo]()
$174
This Delta deal was found by Cheapflights users on 4/6. 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.
Tue 5/195:30 am
GRR
- ORD
1 stop4h 15m
Delta
Tue 5/269:25 am
ORD
- GRR
1 stop3h 15m
Delta
Deal found 4/6![Delta logo]()
$177
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 April 9, 2026.
Search for one-way flight options from Grand Rapids to Chicago. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Southwest deal was found by Cheapflights users on 4/5. 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 5/51:00 pm
GRR
- MDW
Nonstop1h 05m
Southwest
Deal found 4/5![Southwest logo]()
$79
This American Airlines deal was found by Cheapflights users on 4/6. 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 5/268:03 pm
GRR
- ORD
Nonstop1h 42m
American Airlines
Deal found 4/6![American Airlines logo]()
$79
This Delta deal was found by Cheapflights users on 4/5. 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 5/53:50 pm
GRR
- MDW
1 stop3h 08m
Delta
Deal found 4/5![Delta logo]()
$89
This Delta deal was found by Cheapflights users on 4/6. 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.
Tue 5/55:29 am
GRR
- ORD
1 stop5h 50m
Delta
Deal found 4/6![Delta logo]()
$89
This Southwest deal was found by Cheapflights users on 4/4. 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 5/26:45 am
GRR
- MDW
Nonstop1h 00m
Southwest
Deal found 4/4![Southwest logo]()
$96
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Thu 4/305:34 am
GRR
- ORD
Nonstop1h 16m
American Airlines
Deal found 4/6![American Airlines logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:23 pm
GRR
- ORD
1 stop28h 50m
Frontier
Deal found 4/6![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:37 pm
GRR
- ORD
1 stop17h 00m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$102
This Delta deal was found by Cheapflights users on 4/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:55 am
GRR
- ORD
2 stops9h 45m
Delta
Deal found 4/7![Delta logo]()
$104
This Delta deal was found by Cheapflights users on 4/5. 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 5/28:30 am
GRR
- MDW
1 stop5h 13m
Delta
Deal found 4/5![Delta logo]()
$106
This Delta deal was found by Cheapflights users on 4/6. 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.
Thu 4/303:50 pm
GRR
- ORD
1 stop4h 02m
Delta
Deal found 4/6![Delta logo]()
$106
This Delta deal was found by Cheapflights users on 4/4. 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.
Sat 5/27:10 am
GRR
- ORD
2 stops6h 39m
Delta
Deal found 4/4![Delta logo]()
$111
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 April 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (Southwest) |
One-way from | $79 (Southwest) |
Popular in | January |
Cheapest in | October |
Average price | $204 |
Good round-trip deal | $376 or less |
Good one-way deal | $207 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 April 9, 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 - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Mon 5/11
5:40 pm-5:45 pm
Nonstop1h 05m
Chicago Midway
Tue 5/12
9:40 pm-11:35 pm
Nonstop0h 55m
$174
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Tue 5/5
3:50 pm-5:58 pm
1 stop3h 08m
Chicago Midway
Tue 5/12
1:22 pm-5:04 pm
1 stop2h 42m
$177
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Tue 5/19
8:16 am-10:29 am
1 stop3h 13m
Chicago O'Hare Intl
Tue 5/26
7:00 am-11:18 am
1 stop3h 18m
$177
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Tue 5/5
3:50 pm-6:52 pm
1 stop4h 02m
Chicago O'Hare Intl
Tue 5/12
7:00 pm-11:44 pm
1 stop3h 44m
$177
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Tue 6/16
8:11 am-1:04 pm
1 stop5h 53m
Chicago O'Hare Intl
Wed 6/17
7:01 am-2:08 pm
1 stop6h 07m
$177
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Sat 5/2
5:05 pm-5:10 pm
Nonstop1h 05m
Chicago Midway
Sat 5/9
2:15 pm-11:25 pm
2 stops8h 10m
$206
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Thu 5/7
8:16 am-1:01 pm
1 stop5h 45m
Chicago O'Hare Intl
Thu 5/14
7:00 am-1:40 pm
1 stop5h 40m
$211
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Thu 4/30
3:50 pm-6:52 pm
1 stop4h 02m
Chicago O'Hare Intl
Mon 5/11
7:00 pm-11:44 pm
1 stop3h 44m
$231
Grand RapidsChicago
GRR - ORD
GRRORD
Grand Rapids Gerald R. Ford Intl
Mon 6/1
9:09 pm-9:34 pm
Nonstop1h 25m
Chicago O'Hare Intl
Tue 6/2
4:46 pm-7:05 pm
Nonstop1h 19m
$244
Grand RapidsChicago
GRR - MDW
GRRMDW
Grand Rapids Gerald R. Ford Intl
Thu 5/7
8:25 am-12:05 pm
1 stop4h 40m
Chicago Midway
Thu 5/14
3:10 pm-5:05 pm
Nonstop0h 55m
$245
Showing 1-10 of 41 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 April.
| 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, 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 $163). 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 April 9, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 19% 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 April 4, 2026.
Travelers seeking maximum savings on their Grand Rapids to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 9, 2026.
The most flights from GRR to CHI are scheduled on a Thursday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 on average).
How much does it cost to fly round-trip from Grand Rapids to Chicago?
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 April 9, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican 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
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Porter
Benton Harbor
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Other flights to Chicago
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Grand Rapids and Chicago flights
Browse other Grand Rapids and Chicago flight options. Last updated on April 9, 2026.
Other flights from Grand Rapids
Browse through other flights departing from Grand Rapids. Flights are based on user searches made on Cheapflights and were last updated on April 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Grand Rapids to Chicago
Discover the top 2 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 April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$239 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$260 | FlexibilityNo cancel fee | On-time69% |