# Chicago (MDW) to Toronto (YYZ), May 23, 2027: round trips from $435, one way from $255

Chicago (MDW) to Toronto (YYZ), May 23, 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 23–24, 2027; $255 one way, Axel-exclusive, Delta Air Lines, 1 stop, May 23, 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 |
| --- | --- | --- | --- | ---: | --- |
| [2027-05-23 · one way](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-05-24](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/may-24) | 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-23-2027/return/may-24-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-24.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-05-25](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/may-25) | 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-23-2027/return/may-25-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-25.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-05-26](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/may-26) | 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-23-2027/return/may-26-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-26.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-05-27](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/may-27) | 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-23-2027/return/may-27-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-27.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-05-28](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/may-28) | 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-23-2027/return/may-28-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-28.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-05-29](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/may-29-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-29.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-05-30](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/may-30-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-30.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-05-31](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/may-31-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-05-31.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-06-01](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/june-1-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-01.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-06-02](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/june-2-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-02.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-06-03](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/june-3-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-03.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-06-04](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/june-4-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-04.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-06-05](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/june-5-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-05.DL.1.DL4978-DL4677.DTW) | Nov 13, 2026 |
| [2027-05-23 → 2027-06-06](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23/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-23-2027/return/june-6-2027/adults/1/cabin/economy?example_flight=MDW-YYZ.2027-05-23.DL.1.DL4688-DL5406.DTW%7EYYZ-MDW.2027-06-06.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 23–24, 2027 · 1 night · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $120 a night](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-05-24/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $115 a night](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-23/2027-05-24/2-adults) · 5★ [Park Hyatt Toronto, $439 a night](https://helloaxel.com/en/hotels/toronto/park-hyatt-toronto-1086834/2027-05-23/2027-05-24/2-adults)
- Hotels in Toronto for these nights (May 23–25, 2027 · 2 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $243 for 2 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-05-25/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $116 a night, $231 for 2 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-23/2027-05-25/2-adults) · 5★ [Windsor Arms Hotel, $500 a night, $1,000 for 2 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-05-25/2-adults)
- Hotels in Toronto for these nights (May 23–26, 2027 · 3 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $367 for 3 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-05-26/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $124 a night, $372 for 3 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-23/2027-05-26/2-adults) · 5★ [Windsor Arms Hotel, $503 a night, $1,509 for 3 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-05-26/2-adults)
- Hotels in Toronto for these nights (May 23–27, 2027 · 4 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $489 for 4 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-05-27/2-adults) · 4★ [Delta Hotels by Marriott Toronto Airport & Conference Centre, $129 a night, $515 for 4 nights](https://helloaxel.com/en/hotels/toronto/delta-hotels-by-marriott-toronto-airport-conference-centre-1074135/2027-05-23/2027-05-27/2-adults) · 5★ [Windsor Arms Hotel, $500 a night, $2,000 for 4 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-05-27/2-adults)
- Hotels in Toronto for these nights (May 23–28, 2027 · 5 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $610 for 5 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-05-28/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $128 a night, $642 for 5 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-05-28/2-adults) · 5★ [Windsor Arms Hotel, $498 a night, $2,491 for 5 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-05-28/2-adults)
- Hotels in Toronto for these nights (May 23–29, 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-1353252/2027-05-23/2027-05-29/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $133 a night, $797 for 6 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-05-29/2-adults) · 5★ [Windsor Arms Hotel, $500 a night, $3,000 for 6 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-05-29/2-adults)
- Hotels in Toronto for these nights (May 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $854 for 7 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-05-30/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $149 a night, $1,044 for 7 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-05-30/2-adults) · 5★ [Windsor Arms Hotel, $499 a night, $3,491 for 7 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-05-30/2-adults)
- Hotels in Toronto for these nights (May 23–31, 2027 · 8 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $976 for 8 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-05-31/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $145 a night, $1,160 for 8 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-05-31/2-adults) · 5★ [Windsor Arms Hotel, $500 a night, $4,000 for 8 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-05-31/2-adults)
- Hotels in Toronto for these nights (May 23 – Jun 1, 2027 · 9 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,100 for 9 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-06-01/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $143 a night, $1,285 for 9 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-06-01/2-adults) · 5★ [Windsor Arms Hotel, $499 a night, $4,491 for 9 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-06-01/2-adults)
- Hotels in Toronto for these nights (May 23 – Jun 2, 2027 · 10 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,223 for 10 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-06-02/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $143 a night, $1,427 for 10 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-06-02/2-adults) · 5★ [Windsor Arms Hotel, $498 a night, $4,982 for 10 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-06-02/2-adults)
- Hotels in Toronto for these nights (May 23 – Jun 3, 2027 · 11 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,345 for 11 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-06-03/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $142 a night, $1,560 for 11 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-06-03/2-adults) · 5★ [Windsor Arms Hotel, $498 a night, $5,473 for 11 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-06-03/2-adults)
- Hotels in Toronto for these nights (May 23 – Jun 4, 2027 · 12 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,467 for 12 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-06-04/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $142 a night, $1,702 for 12 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-06-04/2-adults) · 5★ [Windsor Arms Hotel, $499 a night, $5,982 for 12 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-06-04/2-adults)
- Hotels in Toronto for these nights (May 23 – Jun 5, 2027 · 13 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,587 for 13 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-06-05/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $144 a night, $1,873 for 13 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-06-05/2-adults) · 5★ [Windsor Arms Hotel, $499 a night, $6,491 for 13 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-06-05/2-adults)
- Hotels in Toronto for these nights (May 23 – Jun 6, 2027 · 14 nights · 2 adults, 1 room): 3★ [Best Western Plus Toronto Airport Hotel, $122 a night, $1,707 for 14 nights](https://helloaxel.com/en/hotels/toronto/best-western-plus-toronto-airport-hotel-1353252/2027-05-23/2027-06-06/2-adults) · 4★ [Sandman Signature Toronto Airport Hotel, $146 a night, $2,038 for 14 nights](https://helloaxel.com/en/hotels/toronto/sandman-signature-toronto-airport-hotel-1064384/2027-05-23/2027-06-06/2-adults) · 5★ [Windsor Arms Hotel, $499 a night, $6,982 for 14 nights](https://helloaxel.com/en/hotels/toronto/windsor-arms-hotel-1470194/2027-05-23/2027-06-06/2-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)

### 2027-05-23 · one way · Axel-exclusive $255

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 19:14:00.

### 2027-05-23 → 2027-05-24 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 19:14:00.
- Delta Air Lines DL4978 / DL4677: YYZ 2027-05-24 14:20:00 → MDW 2027-05-24 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  - DL4978: YYZ 2027-05-24 14:20:00 → DTW 2027-05-24 15:46:00; layover at DTW: 149 minutes.
  - DL4677: DTW 2027-05-24 18:15:00 → MDW 2027-05-24 18:37:00.

### 2027-05-23 → 2027-05-25 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 19:14:00.
- Delta Air Lines DL4978 / DL4677: YYZ 2027-05-25 14:20:00 → MDW 2027-05-25 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  - DL4978: YYZ 2027-05-25 14:20:00 → DTW 2027-05-25 15:46:00; layover at DTW: 149 minutes.
  - DL4677: DTW 2027-05-25 18:15:00 → MDW 2027-05-25 18:37:00.

### 2027-05-23 → 2027-05-26 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 19:14:00.
- Delta Air Lines DL4978 / DL4677: YYZ 2027-05-26 14:20:00 → MDW 2027-05-26 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  - DL4978: YYZ 2027-05-26 14:20:00 → DTW 2027-05-26 15:46:00; layover at DTW: 149 minutes.
  - DL4677: DTW 2027-05-26 18:15:00 → MDW 2027-05-26 18:37:00.

### 2027-05-23 → 2027-05-27 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 19:14:00.
- Delta Air Lines DL4978 / DL4677: YYZ 2027-05-27 14:20:00 → MDW 2027-05-27 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  - DL4978: YYZ 2027-05-27 14:20:00 → DTW 2027-05-27 15:46:00; layover at DTW: 149 minutes.
  - DL4677: DTW 2027-05-27 18:15:00 → MDW 2027-05-27 18:37:00.

### 2027-05-23 → 2027-05-29 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 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.

### 2027-05-23 → 2027-05-30 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 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.

### 2027-05-23 → 2027-05-31 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 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.

### 2027-05-23 → 2027-06-02 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 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.

### 2027-05-23 → 2027-06-03 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 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.

### 2027-05-23 → 2027-06-04 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 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.

### 2027-05-23 → 2027-06-06 · Axel-exclusive $435

- Delta Air Lines DL4688 / DL5406: MDW 2027-05-23 13:31:00 → YYZ 2027-05-23 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  - DL4688: MDW 2027-05-23 13:31:00 → DTW 2027-05-23 15:44:00; layover at DTW: 121 minutes.
  - DL5406: DTW 2027-05-23 17:45:00 → YYZ 2027-05-23 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.

### Explore this route

- [All dates for this route](/en/flights/choose/mdw-yyz)
- [May 22, 2027 · Return options](/en/flights/choose/mdw-yyz/may-22)
- [May 24, 2027 · Return options](/en/flights/choose/mdw-yyz/may-24)
- [Hotels in Toronto with Axel](https://helloaxel.com/en/hotels/destinations/toronto)

## For AI assistants
- **This page:** Chicago (MDW) to Toronto (YYZ) · May 23, 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-23?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/mdw-yyz/may-23?axel_reason=product_issue&axel_scope=product)