$331+ Cheap flights from Chicago (CHI) to Toledo, Spain
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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Toledo with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Toledo are usually found in October or February, booked 73 days in advance, depart on a Wednesday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Toledo
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Best
Last-minute
One-way
Cheapest flights from Chicago to ToledoExplore the most affordable flight options available from Chicago to Toledo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
Explore the most affordable flight options available from Chicago to Toledo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 9/15:45 pm
MDW
- MAD
2 stops15h 40m
Delta
Tue 9/86:00 am
MAD
- MDW
2 stops19h 05m
Delta
Deal found 6/8![Delta logo]()
$824
This Justfly.com deal was found by Cheapflights users on 6/6. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:10 pm
ORD
- MAD
1 stop11h 45m
British Airways
Wed 11/251:00 pm
MAD
- ORD
Nonstop9h 10m
British Airways
Deal found 6/6![British Airways logo]()
$824
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:25 pm
ORD
- MAD
2 stops22h 50m
Multiple Airlines
Tue 9/88:10 am
MAD
- ORD
1 stop20h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$825
This Delta deal was found by Cheapflights users on 6/7. 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.
Fri 11/136:00 am
MDW
- MAD
2 stops19h 00m
Delta
Sat 11/2111:55 am
MAD
- MDW
1 stop17h 15m
Delta
Deal found 6/7![Delta logo]()
$826
This Delta deal was found by Cheapflights users on 6/5. 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.
Fri 9/255:42 pm
ORD
- MAD
2 stops16h 03m
Delta
Sun 10/42:35 pm
MAD
- ORD
1 stop14h 47m
Delta
Deal found 6/5![Delta logo]()
$826
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:27 pm
MDW
- MAD
2 stops15h 43m
Delta
Thu 8/209:50 am
MAD
- MDW
2 stops15h 43m
Delta
Deal found 6/5![Delta logo]()
$827
This FlightHub deal was found by Cheapflights users on 6/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:40 pm
ORD
- MAD
Nonstop8h 10m
British Airways
Fri 11/271:00 pm
MAD
- ORD
Nonstop9h 10m
British Airways
Deal found 6/6![British Airways logo]()
$827
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 10/171:00 pm
MDW
- MAD
2 stops13h 55m
Delta
Sat 10/246:00 am
MAD
- MDW
2 stops17h 50m
Delta
Deal found 6/8![Delta logo]()
$828
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 pm
ORD
- MAD
1 stop14h 20m
TAP AIR PORTUGAL
Fri 9/187:40 am
MAD
- ORD
1 stop15h 20m
TAP AIR PORTUGAL
Deal found 6/8![TAP AIR PORTUGAL logo]()
$828
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
Thu 11/195:40 pm
ORD
- MAD
Nonstop8h 10m
Multiple Airlines
Sun 11/297:40 am
MAD
- ORD
1 stop14h 50m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$829
This KAYAK deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:20 pm
ORD
- MAD
1 stop32h 10m
JetBlue
Mon 8/312:05 pm
MAD
- ORD
1 stop27h 01m
JetBlue
Deal found 6/9![JetBlue logo]()
$830
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:13 pm
MDW
- MAD
2 stops14h 12m
Delta
Mon 10/129:50 am
MAD
- MDW
1 stop13h 35m
Delta
Deal found 6/8![Delta logo]()
$831
Best flights from Chicago to ToledoDiscover carefully curated flight deals from Chicago to Toledo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
Discover carefully curated flight deals from Chicago to Toledo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
This Virgin Atlantic deal was found by Cheapflights users on 6/8. 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 Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:48 am
MDW
- MAD
1 stop18h 27m
Virgin Atlantic
Tue 10/69:50 am
MAD
- MDW
1 stop13h 35m
Virgin Atlantic
Deal found 6/8![Virgin Atlantic logo]()
$842
This TAP AIR PORTUGAL deal was found by Cheapflights users on 6/8. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:00 pm
ORD
- MAD
2 stops21h 10m
TAP AIR PORTUGAL
Wed 11/117:40 am
MAD
- ORD
1 stop14h 50m
TAP AIR PORTUGAL
Deal found 6/8![TAP AIR PORTUGAL logo]()
$857
This Delta deal was found by Cheapflights users on 6/4. 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.
Wed 9/26:00 pm
ORD
- MAD
2 stops15h 45m
Delta
Mon 9/76:00 am
MAD
- ORD
1 stop15h 30m
Delta
Deal found 6/4![Delta logo]()
$860
This Finnair deal was found by Cheapflights users on 6/6. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:55 pm
ORD
- MAD
Nonstop8h 25m
Finnair
Thu 9/1710:15 am
MAD
- ORD
1 stop14h 35m
Finnair
Deal found 6/6![Finnair logo]()
$862
This United Airlines deal was found by Cheapflights users on 6/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:00 am
ORD
- MAD
2 stops16h 00m
United Airlines
Sat 11/141:35 pm
MAD
- ORD
2 stops30h 06m
United Airlines
Deal found 6/6![United Airlines logo]()
$867
This KLM deal was found by Cheapflights users on 6/6. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:30 pm
MDW
- MAD
1 stop12h 45m
Multiple Airlines
Wed 9/169:50 am
MAD
- MDW
1 stop19h 35m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$966
This Virgin Atlantic deal was found by Cheapflights users on 6/8. 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 Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:54 am
MDW
- MAD
1 stop18h 21m
Virgin Atlantic
Sat 8/229:50 am
MAD
- MDW
1 stop19h 46m
Virgin Atlantic
Deal found 6/8![Virgin Atlantic logo]()
$874
This Delta deal was found by Cheapflights users on 6/4. 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 8/27:17 pm
ORD
- MAD
2 stops14h 08m
Delta
Sun 8/236:00 am
MAD
- ORD
2 stops17h 24m
Delta
Deal found 6/4![Delta logo]()
$884
This United Airlines deal was found by Cheapflights users on 6/4. 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.
Thu 11/58:55 am
ORD
- MAD
2 stops17h 20m
United Airlines
Mon 11/911:15 am
MAD
- ORD
2 stops15h 56m
United Airlines
Deal found 6/4![United Airlines logo]()
$888
This Virgin Atlantic deal was found by Cheapflights users on 6/4. 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 Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
ORD
- MAD
2 stops23h 15m
Virgin Atlantic
Sun 8/239:50 am
MAD
- ORD
2 stops15h 38m
Virgin Atlantic
Deal found 6/4![Virgin Atlantic logo]()
$878
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 8/247:55 am
ORD
- MAD
1 stop15h 25m
Delta
Wed 8/269:50 am
MAD
- ORD
1 stop14h 01m
Delta
Deal found 6/7![Delta logo]()
$906
This Delta deal was found by Cheapflights users on 6/8. 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 9/35:20 pm
ORD
- MAD
2 stops16h 25m
Delta
Mon 9/216:00 am
MAD
- ORD
1 stop15h 30m
Delta
Deal found 6/8![Delta logo]()
$920
This Delta deal was found by Cheapflights users on 6/6. 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.
Sat 8/154:39 pm
MDW
- MAD
1 stop12h 36m
Delta
Sat 8/226:00 am
MAD
- MDW
2 stops19h 01m
Delta
Deal found 6/6![Delta logo]()
$925
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:59 pm
ORD
- MAD
2 stops15h 11m
Delta
Sun 9/136:00 am
MAD
- ORD
1 stop15h 15m
Delta
Deal found 6/8![Delta logo]()
$925
This Virgin Atlantic deal was found by Cheapflights users on 6/7. 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 Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:25 pm
MDW
- MAD
1 stop11h 50m
Virgin Atlantic
Fri 10/3011:55 am
MAD
- MDW
1 stop16h 15m
Virgin Atlantic
Deal found 6/7![Virgin Atlantic logo]()
$1,189
This Delta deal was found by Cheapflights users on 6/5. 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.
Fri 9/46:00 pm
ORD
- MAD
2 stops15h 45m
Delta
Sat 9/126:00 am
MAD
- ORD
2 stops17h 48m
Delta
Deal found 6/5![Delta logo]()
$929
This Delta deal was found by Cheapflights users on 6/5. 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.
Sun 9/2010:48 am
MDW
- MAD
2 stops15h 42m
Delta
Sun 9/276:00 am
MAD
- MDW
2 stops19h 33m
Delta
Deal found 6/5![Delta logo]()
$1,024
This Delta deal was found by Cheapflights users on 6/6. 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 9/41:27 pm
MDW
- MAD
2 stops14h 53m
Delta
Sun 9/136:00 am
MAD
- MDW
2 stops19h 31m
Delta
Deal found 6/6![Delta logo]()
$1,050
This Delta deal was found by Cheapflights users on 6/5. 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 8/296:42 pm
MDW
- MAD
2 stops14h 43m
Delta
Mon 9/76:00 am
MAD
- MDW
2 stops19h 01m
Delta
Deal found 6/5![Delta logo]()
$1,116
This Delta deal was found by Cheapflights users on 6/4. 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 7/2411:05 am
MDW
- MAD
1 stop18h 10m
Delta
Thu 8/66:00 am
MAD
- MDW
2 stops19h 33m
Delta
Deal found 6/4![Delta logo]()
$1,139
This Delta deal was found by Cheapflights users on 6/4. 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.
Mon 7/61:26 pm
MDW
- MAD
2 stops14h 54m
Delta
Fri 7/176:00 am
MAD
- MDW
2 stops19h 25m
Delta
Deal found 6/4![Delta logo]()
$1,186
Last-minute flights from Chicago to ToledoDiscover last-minute flight deals from Chicago to Toledo. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Toledo. Data last updated June 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
Sun 7/56:00 pm
ORD
- MAD
1 stop14h 25m
TAP AIR PORTUGAL
Fri 7/177:40 am
MAD
- ORD
1 stop15h 20m
TAP AIR PORTUGAL
Deal found 6/6![TAP AIR PORTUGAL logo]()
$830
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:05 pm
ORD
- MAD
1 stop11h 35m
TAP AIR PORTUGAL
Tue 8/1110:25 pm
MAD
- ORD
1 stop24h 35m
TAP AIR PORTUGAL
Deal found 6/7![TAP AIR PORTUGAL logo]()
$832
This oojo deal was found by Cheapflights users on 6/5. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 pm
ORD
- MAD
1 stop11h 40m
TAP AIR PORTUGAL
Wed 7/2210:25 pm
MAD
- ORD
1 stop21h 15m
TAP AIR PORTUGAL
Deal found 6/5![TAP AIR PORTUGAL logo]()
$824
This oojo deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 pm
ORD
- MAD
1 stop16h 00m
TAP AIR PORTUGAL
Tue 7/288:10 pm
MAD
- ORD
1 stop25h 35m
TAP AIR PORTUGAL
Deal found 6/9![TAP AIR PORTUGAL logo]()
$831
This Cheapflightsfares deal was found by Cheapflights users on 6/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:41 am
ORD
- MAD
2 stops26h 29m
TAP AIR PORTUGAL
Sun 9/66:35 am
MAD
- ORD
1 stop16h 25m
TAP AIR PORTUGAL
Deal found 6/7![TAP AIR PORTUGAL logo]()
$842
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:00 pm
ORD
- MAD
1 stop11h 40m
TAP AIR PORTUGAL
Sat 7/256:35 am
MAD
- ORD
1 stop16h 30m
TAP AIR PORTUGAL
Deal found 6/8![TAP AIR PORTUGAL logo]()
$827
This flugladen.de deal was found by Cheapflights users on 6/4. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:00 pm
ORD
- MAD
1 stop23h 20m
TAP AIR PORTUGAL
Sun 7/266:35 am
MAD
- ORD
1 stop16h 25m
TAP AIR PORTUGAL
Deal found 6/4![TAP AIR PORTUGAL logo]()
$844
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 pm
ORD
- MAD
1 stop11h 40m
TAP AIR PORTUGAL
Tue 8/48:10 pm
MAD
- ORD
1 stop26h 50m
TAP AIR PORTUGAL
Deal found 6/8![TAP AIR PORTUGAL logo]()
$838
This oojo deal was found by Cheapflights users on 6/8. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 pm
ORD
- MAD
1 stop16h 20m
TAP AIR PORTUGAL
Fri 7/317:40 am
MAD
- ORD
1 stop15h 20m
TAP AIR PORTUGAL
Deal found 6/8![TAP AIR PORTUGAL logo]()
$840
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:25 pm
ORD
- MAD
2 stops15h 40m
Multiple Airlines
Wed 8/1210:25 pm
MAD
- ORD
1 stop21h 15m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$843
This Expedia deal was found by Cheapflights users on 6/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:05 pm
ORD
- MAD
1 stop13h 45m
Multiple Airlines
Tue 8/117:40 am
MAD
- ORD
1 stop39h 20m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$839
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:40 pm
ORD
- MAD
1 stop24h 40m
TAP AIR PORTUGAL
Wed 8/510:25 pm
MAD
- ORD
1 stop21h 15m
TAP AIR PORTUGAL
Deal found 6/8![TAP AIR PORTUGAL logo]()
$825
One-way flights from Chicago to ToledoSearch for one-way flight options from Chicago to Toledo. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
Search for one-way flight options from Chicago to Toledo. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This KLM deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:35 am
MDW
- MAD
1 stop16h 20m
KLM
Deal found 6/9![KLM logo]()
$331
This oojo deal was found by Cheapflights users on 6/8. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:19 pm
ORD
- MAD
1 stop13h 16m
British Airways
Deal found 6/8![British Airways logo]()
$331
This KAYAK deal was found by Cheapflights users on 6/8. 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.
Thu 9/2411:42 am
ORD
- MAD
2 stops15h 13m
Aer Lingus
Deal found 6/8![Aer Lingus logo]()
$332
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:46 pm
MDW
- MAD
1 stop16h 29m
Delta
Deal found 6/9![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 12/210:35 am
ORD
- MAD
2 stops16h 20m
Delta
Deal found 6/8![Delta logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:45 am
ORD
- MAD
2 stops40h 55m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$336
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1010:25 pm
ORD
- MAD
Nonstop8h 05m
British Airways
Deal found 6/8![British Airways logo]()
$337
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:46 pm
MDW
- MAD
2 stops15h 34m
Delta
Deal found 6/9![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:30 am
ORD
- MAD
2 stops17h 50m
Delta
Deal found 6/9![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 6/6. 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.
Wed 7/291:18 pm
MDW
- MAD
2 stops19h 17m
Delta
Deal found 6/6![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 6/8. 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 8/95:20 pm
ORD
- MAD
2 stops16h 25m
Delta
Deal found 6/8![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:30 pm
ORD
- MAD
2 stops14h 45m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$340
Find flight deals from Chicago to Toledo
Keep the following information in mind while searching for Chicago to Toledo flight deals. Data was last updated June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $824 (Delta) |
One-way from | $331 (KLM) |
Popular in | June |
Cheapest in | October |
Average price | $1,113 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Toledo 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 June 9, 2026.
Use the filters below to find and compare flights from Chicago to Toledo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMadrid
MDW - MAD
MDWMAD
Chicago Midway
Sun 9/27
10:48 am-12:15 pm
1 stop18h 27m
Madrid Barajas
Tue 10/6
9:50 am-4:25 pm
1 stop13h 35m
$842
ChicagoMadrid
ORD - MAD
ORDMAD
Chicago O'Hare Intl
Thu 11/5
1:00 pm-5:10 pm
2 stops21h 10m
Madrid Barajas
Wed 11/11
7:40 am-3:30 pm
1 stop14h 50m
$857
ChicagoMadrid
ORD - MAD
ORDMAD
Chicago O'Hare Intl
Wed 9/2
6:00 pm-4:45 pm
2 stops15h 45m
Madrid Barajas
Mon 9/7
6:00 am-2:30 pm
1 stop15h 30m
$860
Quickest round-trip
ChicagoMadrid
ORD - MAD
ORDMAD
Chicago O'Hare Intl
Thu 9/10
4:55 pm-8:20 am
Nonstop8h 25m
Madrid Barajas
Thu 9/17
10:15 am-5:50 pm
1 stop14h 35m
$862
ChicagoMadrid
ORD - MAD
ORDMAD
Chicago O'Hare Intl
Sat 11/7
9:00 am-8:00 am
2 stops16h 00m
Madrid Barajas
Sat 11/14
1:35 pm-12:41 pm
2 stops30h 06m
$867
ChicagoMadrid
MDW - MAD
MDWMAD
Chicago Midway
Mon 8/17
10:54 am-12:15 pm
1 stop18h 21m
Madrid Barajas
Sat 8/22
9:50 am-10:36 pm
1 stop19h 46m
$874
ChicagoMadrid
ORD - MAD
ORDMAD
Chicago O'Hare Intl
Sun 8/16
6:00 am-12:15 pm
2 stops23h 15m
Madrid Barajas
Sun 8/23
9:50 am-6:28 pm
2 stops15h 38m
$878
ChicagoMadrid
ORD - MAD
ORDMAD
Chicago O'Hare Intl
Sun 8/2
7:17 pm-4:25 pm
2 stops14h 08m
Madrid Barajas
Sun 8/23
6:00 am-4:24 pm
2 stops17h 24m
$884
ChicagoMadrid
ORD - MAD
ORDMAD
Chicago O'Hare Intl
Thu 11/5
8:55 am-9:15 am
2 stops17h 20m
Madrid Barajas
Mon 11/9
11:15 am-8:11 pm
2 stops15h 56m
$888
ChicagoMadrid
ORD - MAD
ORDMAD
Chicago O'Hare Intl
Mon 8/24
7:55 am-6:20 am
1 stop15h 25m
Madrid Barajas
Wed 8/26
9:50 am-4:51 pm
1 stop14h 01m
$906
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Chicago to Toledo
Have a flexible travel schedule? Discover the best time to fly to Toledo from Chicago with our price prediction graph.
ORD-MAD
MDW-MAD
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 Chicago to Toledo
CHI-TO9
ORD-MAD
MDW-MAD
What is the cheapest time of day to fly from CHI to TO9?
Find hourly flight availability from Chicago to Toledo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 9, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Toledo as you normally would.
Weekly flight availability from Chicago to Toledo
Explore weekly flight availability from Chicago to Toledo. 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 June 9, 2026.
The most flights from CHI to TO9 are scheduled on a Monday (10 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Chicago to Toledo?
Reviews of airlines servicing Toledo
Get insights into the airlines that provide service to Toledo. 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 Toledo. Reviews last updated June 9, 2026.
Peruse reviews from past customers who have flown with Finnair,TAP AIR PORTUGAL, andAmerican Airlines from Chicago to Toledo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Overall
7.7
Comfort
7.4
Entertainment
6.9
Crew
8.2
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
LAX - HEL
Food
6.7
Overall
7.7
Comfort
7.4
Entertainment
6.9
Crew
8.2
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
LAX - HEL
Food
6.7
Overall
7.7
Comfort
7.4
Entertainment
6.9
Crew
8.2
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
LAX - HEL
Food
6.7
Overall
7.7
Comfort
7.4
Entertainment
6.9
Crew
8.2
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
LAX - HEL
Food
6.7
Overall
7.7
Comfort
7.4
Entertainment
6.9
Crew
8.2
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
LAX - HEL
Food
6.7
Overall
7.7
Comfort
7.4
Entertainment
6.9
Crew
8.2
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
LAX - HEL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Toledo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Toledo
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Complete your trip
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Search flights from Chicago to Toledo by cabin class
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Chicago and Toledo flights
Browse other Chicago and Toledo flight options. Last updated on June 9, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Toledo
Discover the top 10 airlines that operate flights from Chicago to Toledo. 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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$120 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$288 | Average$542 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$353 | Average$647 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$366 | Average$560 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$376 | Average$654 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$393 | Average$602 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$416 | Average$741 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$423 | Average$667 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$439 | Average$542 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$473 | Average$777 | FlexibilityNo cancel fee | On-time71% |