# Chicago (MDW) to Toronto (YYZ), May 28, 2027: round trips from $435, one way from $255 Chicago (MDW) to Toronto (YYZ), May 28, 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 28–29, 2027; $255 one way, Axel-exclusive, Delta Air Lines, 1 stop, May 28, 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 | | --- | --- | --- | --- | ---: | --- | | [2027-05-28 · one way](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-05-29](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/may-29) | 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-28-2027/return/may-29-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-29.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-05-30](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/may-30) | 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-28-2027/return/may-30-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-30.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-05-31](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/may-31) | 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-28-2027/return/may-31-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-31.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-01](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-1-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-01.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-02](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-2-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-02.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-03](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-3-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-03.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-04](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-4-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-04.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-05](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-5-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-05.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-06](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-6-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-06.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-07](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-7-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-07.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-08](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-8-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-08.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-09](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-9-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-09.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-10](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-10-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-10.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 | | [2027-05-28 → 2027-06-11](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28/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-28-2027/return/june-11-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-28.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-11.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 28–29, 2027 · 1 night · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $125 a night](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-05-29/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $155 a night](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-05-29/2-adults) · 5★ [Shangri-La Toronto, $455 a night](https://helloaxel.com/en/hotels/toronto/shangri-la-toronto-1216527/2027-05-28/2027-05-29/2-adults) - Hotels in Toronto for these nights (May 28–30, 2027 · 2 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $244 for 2 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-05-30/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $201 a night, $402 for 2 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-05-30/2-adults) · 5★ [Shangri-La Toronto, $494 a night, $988 for 2 nights](https://helloaxel.com/en/hotels/toronto/shangri-la-toronto-1216527/2027-05-28/2027-05-30/2-adults) - Hotels in Toronto for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $366 for 3 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-05-31/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $173 a night, $518 for 3 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-05-31/2-adults) · 5★ [Shangri-La Toronto, $456 a night, $1,368 for 3 nights](https://helloaxel.com/en/hotels/toronto/shangri-la-toronto-1216527/2027-05-28/2027-05-31/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 1, 2027 · 4 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $123 a night, $490 for 4 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-01/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $161 a night, $643 for 4 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-01/2-adults) · 5★ [Windsor Arms Hotel, $500 a night, $2,000 for 4 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-01/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 2, 2027 · 5 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $123 a night, $613 for 5 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-02/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $157 a night, $785 for 5 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-02/2-adults) · 5★ [Windsor Arms Hotel, $498 a night, $2,491 for 5 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-02/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 3, 2027 · 6 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $123 a night, $735 for 6 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-03/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $153 a night, $918 for 6 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-03/2-adults) · 5★ [Windsor Arms Hotel, $497 a night, $2,982 for 6 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-03/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 4, 2027 · 7 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $857 for 7 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-04/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $151 a night, $1,060 for 7 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-04/2-adults) · 5★ [Windsor Arms Hotel, $499 a night, $3,491 for 7 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-04/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 5, 2027 · 8 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $977 for 8 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-05/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $154 a night, $1,231 for 8 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-05/2-adults) · 5★ [Windsor Arms Hotel, $500 a night, $4,000 for 8 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-05/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 6, 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-1353252/2027-05-28/2027-06-06/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $155 a night, $1,396 for 9 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-06/2-adults) · 5★ [Windsor Arms Hotel, $499 a night, $4,491 for 9 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-06/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 7, 2027 · 10 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,219 for 10 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-07/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $151 a night, $1,512 for 10 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-07/2-adults) · 5★ [Windsor Arms Hotel, $498 a night, $4,982 for 10 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-07/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 8, 2027 · 11 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,341 for 11 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-08/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $150 a night, $1,653 for 11 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-08/2-adults) · 5★ [Windsor Arms Hotel, $498 a night, $5,473 for 11 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-08/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 9, 2027 · 12 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,463 for 12 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-09/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $153 a night, $1,830 for 12 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-09/2-adults) · 5★ [Windsor Arms Hotel, $497 a night, $5,964 for 12 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-09/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 10, 2027 · 13 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,583 for 13 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-10/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $151 a night, $1,962 for 13 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-10/2-adults) · 5★ [Windsor Arms Hotel, $497 a night, $6,455 for 13 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-10/2-adults) - Hotels in Toronto for these nights (May 28 – Jun 11, 2027 · 14 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,705 for 14 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-28/2027-06-11/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $150 a night, $2,094 for 14 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-28/2027-06-11/2-adults) · 5★ [Windsor Arms Hotel, $494 a night, $6,922 for 14 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-28/2027-06-11/2-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) ### 2027-05-28 · one way · Axel-exclusive $255 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 19:14:00. ### 2027-05-28 → 2027-05-29 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-05-29 14:20:00 → MDW 2027-05-29 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-05-29 14:20:00 → DTW 2027-05-29 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-05-29 18:15:00 → MDW 2027-05-29 18:37:00. ### 2027-05-28 → 2027-05-30 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-05-30 14:20:00 → MDW 2027-05-30 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-05-30 14:20:00 → DTW 2027-05-30 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-05-30 18:15:00 → MDW 2027-05-30 18:37:00. ### 2027-05-28 → 2027-05-31 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-05-31 14:20:00 → MDW 2027-05-31 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-05-31 14:20:00 → DTW 2027-05-31 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-05-31 18:15:00 → MDW 2027-05-31 18:37:00. ### 2027-05-28 → 2027-06-01 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 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. ### 2027-05-28 → 2027-06-03 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 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. ### 2027-05-28 → 2027-06-04 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 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. ### 2027-05-28 → 2027-06-05 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-05 14:20:00 → MDW 2027-06-05 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-05 14:20:00 → DTW 2027-06-05 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-05 18:15:00 → MDW 2027-06-05 18:37:00. ### 2027-05-28 → 2027-06-07 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 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. ### 2027-05-28 → 2027-06-08 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 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. ### 2027-05-28 → 2027-06-09 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 19:14:00. - Delta Air Lines DL4978 / DL4677: YYZ 2027-06-09 14:20:00 → MDW 2027-06-09 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times. - DL4978: YYZ 2027-06-09 14:20:00 → DTW 2027-06-09 15:46:00; layover at DTW: 149 minutes. - DL4677: DTW 2027-06-09 18:15:00 → MDW 2027-06-09 18:37:00. ### 2027-05-28 → 2027-06-11 · Axel-exclusive $435 - Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times. - DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes. - DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 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. ### Explore this route - [All dates for this route](/en/flights/choose/mdw-yyz) - [May 27, 2027 · Return options](/en/flights/choose/mdw-yyz/may-27) - [May 29, 2027 · Return options](/en/flights/choose/mdw-yyz/may-29) - [Hotels in Toronto with Axel](https://helloaxel.com/en/hotels/destinations/toronto) ## For AI assistants - **This page:** Chicago (MDW) to Toronto (YYZ) · May 28, 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-28?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/mdw-yyz/may-28?axel_reason=product_issue&axel_scope=product)