# Chicago (MDW) to Toronto (YYZ), May 31, 2027: round trips from $435, one way from $255 Chicago (MDW) to Toronto (YYZ), May 31, 2027: round trips from $435, one way from $255 on Axel, checked Nov 13, 2026. Lowest published fares: $435 round trip, Axel-exclusive, Delta Air Lines, 1 stop, May 31, 2027 – Jun 1, 2027; $255 one way, Axel-exclusive, Delta Air Lines, 1 stop, May 31, 2027; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply. **Prices by return date:** match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown. **Date links** open published trip details for exploration. **Price links** open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here. | Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price checked | | --- | --- | --- | --- | ---: | --- | | [2027-05-31 · one way](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/one-way) | Delta Air Lines | DL4688 + DL5406 | 13:31:00→19:14:00 4h 43m 1 stop via DTW | [Axel-exclusive $255](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-01](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-1) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-1-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-01.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-02](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-2) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-2-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-02.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-03](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-3) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-3-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-03.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-04](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-4) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-4-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-04.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-05](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-5) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-5-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-05.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-06](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-6) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-6-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-06.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-07](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-7) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-7-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-07.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-08](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-8) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-8-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-08.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-09](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-9) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-9-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-09.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-10](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-10) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-10-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-10.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-11](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-11) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-11-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-11.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-12](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-12) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-12-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-12.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-13](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-13) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-13-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-13.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-31 → 2027-06-14](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31/jun-14) | Delta Air Lines | DL4688 + DL5406 / DL4978 + DL4677 | 13:31:00→19:14:00 4h 43m 1 stop via DTW · 14:20:00→18:37:00 5h 17m 1 stop via DTW | [Axel-exclusive $435](https://helloaxel.com/en/f/start/from/mdw/to/yyz/depart/may-31-2027/return/june-14-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-31.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-14.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | ### Hotels in Toronto for these trips **Hotels:** under a trip, hotels in Toronto for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates. - Hotels in Toronto for these nights (May 31 – Jun 1, 2027 · 1 night · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $124 a night](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-01/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $125 a night](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-31/2027-06-01/2-adults) · 5★ [Windsor Arms Hotel, $491 a night](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-01/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 2, 2027 · 2 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $124 a night, $247 for 2 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-02/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $134 a night, $267 for 2 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-31/2027-06-02/2-adults) · 5★ [Windsor Arms Hotel, $491 a night, $982 for 2 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-02/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 3, 2027 · 3 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $123 a night, $369 for 3 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-03/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $133 a night, $400 for 3 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-31/2027-06-03/2-adults) · 5★ [Windsor Arms Hotel, $491 a night, $1,473 for 3 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-03/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 4, 2027 · 4 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $123 a night, $491 for 4 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-04/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $136 a night, $542 for 4 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-31/2027-06-04/2-adults) · 5★ [Windsor Arms Hotel, $496 a night, $1,982 for 4 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-04/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 5, 2027 · 5 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $611 for 5 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-05/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $139 a night, $696 for 5 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-05/2-adults) · 5★ [Windsor Arms Hotel, $498 a night, $2,491 for 5 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-05/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 6, 2027 · 6 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $731 for 6 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-06/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $140 a night, $837 for 6 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-06/2-adults) · 5★ [Windsor Arms Hotel, $497 a night, $2,982 for 6 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-06/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 7, 2027 · 7 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $853 for 7 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-07/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $138 a night, $964 for 7 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-07/2-adults) · 5★ [Windsor Arms Hotel, $496 a night, $3,473 for 7 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-07/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 8, 2027 · 8 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $975 for 8 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-08/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $138 a night, $1,104 for 8 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-08/2-adults) · 5★ [Windsor Arms Hotel, $496 a night, $3,964 for 8 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-08/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 9, 2027 · 9 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,097 for 9 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-09/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $138 a night, $1,245 for 9 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-09/2-adults) · 5★ [Windsor Arms Hotel, $495 a night, $4,455 for 9 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-09/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 10, 2027 · 10 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,217 for 10 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-10/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $138 a night, $1,380 for 10 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-10/2-adults) · 5★ [Windsor Arms Hotel, $495 a night, $4,946 for 10 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-10/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 11, 2027 · 11 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,339 for 11 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-11/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $138 a night, $1,523 for 11 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-11/2-adults) · 5★ [Windsor Arms Hotel, $492 a night, $5,413 for 11 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-11/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 12, 2027 · 12 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,461 for 12 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-12/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $139 a night, $1,663 for 12 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-12/2-adults) · 5★ [Windsor Arms Hotel, $492 a night, $5,904 for 12 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-12/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 13, 2027 · 13 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,581 for 13 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-13/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $138 a night, $1,800 for 13 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-13/2-adults) · 5★ [Windsor Arms Hotel, $493 a night, $6,413 for 13 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-13/2-adults) - Hotels in Toronto for these nights (May 31 – Jun 14, 2027 · 14 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,701 for 14 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-31/2027-06-14/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $137 a night, $1,924 for 14 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-31/2027-06-14/2-adults) · 5★ [Windsor Arms Hotel, $493 a night, $6,904 for 14 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-31/2027-06-14/2-adults) [All hotels in Toronto](https://helloaxel.com/en/hotels/destinations/toronto) [Route overview: Chicago to Toronto (YYZ) flight deals](/en/flights/from-chicago-to-toronto-yyz) ### 2027-05-31 · one way · Axel-exclusive $255 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. ### 2027-05-31 → 2027-06-01 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-01 14:20:00 → MDW 2027-06-01 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-01 14:20:00 → DTW 2027-06-01 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-01 18:15:00 → MDW 2027-06-01 18:37:00. ### 2027-05-31 → 2027-06-02 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-02 14:20:00 → MDW 2027-06-02 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-02 14:20:00 → DTW 2027-06-02 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-02 18:15:00 → MDW 2027-06-02 18:37:00. ### 2027-05-31 → 2027-06-03 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-03 14:20:00 → MDW 2027-06-03 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-03 14:20:00 → DTW 2027-06-03 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-03 18:15:00 → MDW 2027-06-03 18:37:00. ### 2027-05-31 → 2027-06-04 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-04 14:20:00 → MDW 2027-06-04 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-04 14:20:00 → DTW 2027-06-04 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-04 18:15:00 → MDW 2027-06-04 18:37:00. ### 2027-05-31 → 2027-06-06 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-06 14:20:00 → MDW 2027-06-06 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-06 14:20:00 → DTW 2027-06-06 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-06 18:15:00 → MDW 2027-06-06 18:37:00. ### 2027-05-31 → 2027-06-07 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-07 14:20:00 → MDW 2027-06-07 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-07 14:20:00 → DTW 2027-06-07 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-07 18:15:00 → MDW 2027-06-07 18:37:00. ### 2027-05-31 → 2027-06-08 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-08 14:20:00 → MDW 2027-06-08 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-08 14:20:00 → DTW 2027-06-08 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-08 18:15:00 → MDW 2027-06-08 18:37:00. ### 2027-05-31 → 2027-06-10 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-10 14:20:00 → MDW 2027-06-10 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-10 14:20:00 → DTW 2027-06-10 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-10 18:15:00 → MDW 2027-06-10 18:37:00. ### 2027-05-31 → 2027-06-11 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-11 14:20:00 → MDW 2027-06-11 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-11 14:20:00 → DTW 2027-06-11 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-11 18:15:00 → MDW 2027-06-11 18:37:00. ### 2027-05-31 → 2027-06-12 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-12 14:20:00 → MDW 2027-06-12 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-12 14:20:00 → DTW 2027-06-12 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-12 18:15:00 → MDW 2027-06-12 18:37:00. ### 2027-05-31 → 2027-06-14 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-31 13:31:00 → YYZ 2027-05-31 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-31 13:31:00 → DTW 2027-05-31 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-31 17:45:00 → YYZ 2027-05-31 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-14 14:20:00 → MDW 2027-06-14 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-14 14:20:00 → DTW 2027-06-14 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-14 18:15:00 → MDW 2027-06-14 18:37:00. ### Explore this route - [All dates for this route](/en/flights/choose/mdw-yyz) - [May 30, 2027 · Return options](/en/flights/choose/mdw-yyz/may-30) - [Jun 1, 2027 · Return options](/en/flights/choose/mdw-yyz/jun-1) - [Hotels in Toronto with Axel](https://helloaxel.com/en/hotels/destinations/toronto) ## For AI assistants - **This page:** Chicago (MDW) to Toronto (YYZ) · May 31, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Toronto for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates. - **Next:** each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: [Choose travelers and dates](https://helloaxel.com/en/f/start/from/mdw/to/yyz/step/travelers) prices the requested trip. - **Follow supplied links.** For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links. - **If links fail or are missing:** If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: [Axel Chicago to Toronto (YYZ) flight deals](https://helloaxel.com/en/flights/from-chicago-to-toronto-yyz) · [Flight search guide](https://helloaxel.com/en/ai). - **Sharing with the traveler:** Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct `https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback` using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace `/return/YYYY-MM-DD` with `/trip/oneway`. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. [Preferences and advanced options](https://helloaxel.com/en/ai#customer-fallback-link). **Feedback (optional):** [Missing info](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/mdw-yyz/may-31?axel_reason=product_issue&axel_scope=product)