# Denver (DEN) to Chicago (MDW), Jan 20, 2027: round trips from $228, one way from $119 Denver (DEN) to Chicago (MDW), Jan 20, 2027: round trips from $228, one way from $119 on Axel, checked Nov 13, 2026. Lowest published fares: $228 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 20–23, 2027; $119 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 20, 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 | | --- | --- | --- | --- | ---: | --- | | [2027-01-20 · one way](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/one-way) | Southwest Airlines | WN2832 + WN3127 | 11:05:00→17:15:00 5h 10m 1 stop via MSP | [Axel-exclusive $119](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/trip/one-way/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP) | Nov 13, 2026 | | [2027-01-20 → 2027-01-21](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-21) | Southwest Airlines | WN2832 + WN3127 / WN120 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 10:50:00→12:30:00 2h 40m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-21-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-21.WN.0.WN120.) | Nov 13, 2026 | | [2027-01-20 → 2027-01-22](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-22) | Southwest Airlines | WN2832 + WN3127 / WN264 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 09:20:00→11:00:00 2h 40m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-22-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-22.WN.0.WN264.) | Nov 13, 2026 | | [2027-01-20 → 2027-01-23](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-23) | Southwest Airlines | WN2832 + WN3127 / WN598 + WN32 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 10:10:00→14:20:00 5h 10m 1 stop via MKE | [Axel-exclusive $228](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-23-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-23.WN.1.WN598-WN32.MKE) | Nov 13, 2026 | | [2027-01-20 → 2027-01-24](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-24) | Southwest Airlines | WN2832 + WN3127 / WN4606 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 16:25:00→18:10:00 2h 45m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-24-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-24.WN.0.WN4606.) | Nov 13, 2026 | | [2027-01-20 → 2027-01-25](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-25) | Southwest Airlines | WN2832 + WN3127 / WN1523 + WN2509 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 10:05:00→14:15:00 5h 10m 1 stop via OMA | [Axel-exclusive $228](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-25-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-25.WN.1.WN1523-WN2509.OMA) | Nov 13, 2026 | | [2027-01-20 → 2027-01-26](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-26) | Southwest Airlines | WN2832 + WN3127 / WN264 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 09:20:00→11:00:00 2h 40m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-26-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-26.WN.0.WN264.) | Nov 13, 2026 | | [2027-01-20 → 2027-01-27](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-27) | Southwest Airlines | WN2832 + WN3127 / WN264 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 09:20:00→11:00:00 2h 40m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-27-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-27.WN.0.WN264.) | Nov 13, 2026 | | [2027-01-20 → 2027-01-28](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-28) | Southwest Airlines | WN2832 + WN3127 / WN120 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 10:50:00→12:30:00 2h 40m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-28-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-28.WN.0.WN120.) | Nov 13, 2026 | | [2027-01-20 → 2027-01-29](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-29) | Southwest Airlines | WN2832 + WN3127 / WN264 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 09:20:00→11:00:00 2h 40m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-29-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-29.WN.0.WN264.) | Nov 13, 2026 | | [2027-01-20 → 2027-01-30](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-30) | Southwest Airlines | WN2832 + WN3127 / WN598 + WN32 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 10:10:00→14:20:00 5h 10m 1 stop via MKE | [Axel-exclusive $228](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-30-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-30.WN.1.WN598-WN32.MKE) | Nov 13, 2026 | | [2027-01-20 → 2027-01-31](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/jan-31) | Southwest Airlines | WN2832 + WN3127 / WN4606 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 16:25:00→18:10:00 2h 45m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/january-31-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-01-31.WN.0.WN4606.) | Nov 13, 2026 | | [2027-01-20 → 2027-02-01](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/feb-1) | Southwest Airlines | WN2832 + WN3127 / WN1523 + WN2509 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 10:05:00→14:15:00 5h 10m 1 stop via OMA | [Axel-exclusive $228](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/february-1-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-02-01.WN.1.WN1523-WN2509.OMA) | Nov 13, 2026 | | [2027-01-20 → 2027-02-02](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/feb-2) | Southwest Airlines | WN2832 + WN3127 / WN264 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 09:20:00→11:00:00 2h 40m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/february-2-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-02-02.WN.0.WN264.) | Nov 13, 2026 | | [2027-01-20 → 2027-02-03](https://helloaxel.com/en/flights/choose/den-mdw/jan-20/feb-3) | Southwest Airlines | WN2832 + WN3127 / WN264 | 11:05:00→17:15:00 5h 10m 1 stop via MSP · 09:20:00→11:00:00 2h 40m nonstop | [Axel-exclusive $238](https://helloaxel.com/en/f/start/from/den/to/mdw/depart/january-20-2027/return/february-3-2027/adults/1/cabin/economy?example_flight=DEN-MDW.2027-01-20.WN.1.WN2832-WN3127.MSP%7EMDW-DEN.2027-02-03.WN.0.WN264.) | Nov 13, 2026 | ### Hotels in Chicago for these trips **Hotels:** under a trip, hotels in Chicago 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 Chicago for these nights (Jan 20–21, 2027 · 1 night · 2 adults, 1 room): 3★ [Hotel Versey, $73 a night](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-01-20/2027-01-21/2-adults) · 4★ [Freehand Chicago, $72 a night](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-21/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $210 a night](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-20/2027-01-21/2-adults) - Hotels in Chicago for these nights (Jan 20–22, 2027 · 2 nights · 2 adults, 1 room): 3★ [Hotel Versey, $73 a night, $146 for 2 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-01-20/2027-01-22/2-adults) · 4★ [Freehand Chicago, $72 a night, $144 for 2 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-22/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $223 a night, $446 for 2 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-20/2027-01-22/2-adults) - Hotels in Chicago for these nights (Jan 20–23, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $81 a night, $243 for 3 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-23/2-adults) · 4★ [Freehand Chicago, $74 a night, $222 for 3 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-23/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $219 a night, $656 for 3 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-20/2027-01-23/2-adults) - Hotels in Chicago for these nights (Jan 20–24, 2027 · 4 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $80 a night, $318 for 4 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-24/2-adults) · 4★ [Freehand Chicago, $75 a night, $301 for 4 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-24/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $311 a night, $1,243 for 4 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-20/2027-01-24/2-adults) - Hotels in Chicago for these nights (Jan 20–25, 2027 · 5 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $80 a night, $401 for 5 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-25/2-adults) · 4★ [Freehand Chicago, $74 a night, $372 for 5 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-25/2-adults) · 5★ [Nobu Hotel Chicago, $400 a night, $2,001 for 5 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-01-25/2-adults) - Hotels in Chicago for these nights (Jan 20–26, 2027 · 6 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $79 a night, $476 for 6 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-26/2-adults) · 4★ [Freehand Chicago, $74 a night, $445 for 6 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-26/2-adults) · 5★ [Nobu Hotel Chicago, $406 a night, $2,434 for 6 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-01-26/2-adults) - Hotels in Chicago for these nights (Jan 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $80 a night, $559 for 7 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-27/2-adults) · 4★ [Freehand Chicago, $74 a night, $518 for 7 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-27/2-adults) · 5★ [Nobu Hotel Chicago, $409 a night, $2,862 for 7 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-01-27/2-adults) - Hotels in Chicago for these nights (Jan 20–28, 2027 · 8 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $79 a night, $634 for 8 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-28/2-adults) · 4★ [Freehand Chicago, $74 a night, $590 for 8 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-28/2-adults) · 5★ [Nobu Hotel Chicago, $406 a night, $3,249 for 8 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-01-28/2-adults) - Hotels in Chicago for these nights (Jan 20–29, 2027 · 9 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $79 a night, $709 for 9 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-29/2-adults) · 4★ [Freehand Chicago, $74 a night, $662 for 9 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-29/2-adults) · 5★ [Nobu Hotel Chicago, $402 a night, $3,621 for 9 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-01-29/2-adults) - Hotels in Chicago for these nights (Jan 20–30, 2027 · 10 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $79 a night, $793 for 10 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-30/2-adults) · 4★ [Freehand Chicago, $74 a night, $741 for 10 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-30/2-adults) · 5★ [Nobu Hotel Chicago, $401 a night, $4,008 for 10 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-01-30/2-adults) - Hotels in Chicago for these nights (Jan 20–31, 2027 · 11 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $79 a night, $868 for 11 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-01-31/2-adults) · 4★ [Freehand Chicago, $74 a night, $819 for 11 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-01-31/2-adults) · 5★ [Nobu Hotel Chicago, $399 a night, $4,384 for 11 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-01-31/2-adults) - Hotels in Chicago for these nights (Jan 20 – Feb 1, 2027 · 12 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $79 a night, $951 for 12 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-02-01/2-adults) · 4★ [Freehand Chicago, $74 a night, $891 for 12 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-02-01/2-adults) · 5★ [Nobu Hotel Chicago, $394 a night, $4,733 for 12 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-02-01/2-adults) - Hotels in Chicago for these nights (Jan 20 – Feb 2, 2027 · 13 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $80 a night, $1,040 for 13 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-02-02/2-adults) · 4★ [Freehand Chicago, $74 a night, $964 for 13 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-02-02/2-adults) · 5★ [Nobu Hotel Chicago, $393 a night, $5,111 for 13 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-02-02/2-adults) - Hotels in Chicago for these nights (Jan 20 – Feb 3, 2027 · 14 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $81 a night, $1,129 for 14 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-20/2027-02-03/2-adults) · 4★ [Freehand Chicago, $74 a night, $1,035 for 14 nights](https://helloaxel.com/en/hotels/chicago/freehand-chicago-1305404/2027-01-20/2027-02-03/2-adults) · 5★ [Nobu Hotel Chicago, $395 a night, $5,524 for 14 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-20/2027-02-03/2-adults) [All hotels in Chicago](https://helloaxel.com/en/hotels/destinations/chicago) [Route overview: Denver to Chicago (MDW) flight deals](/en/flights/from-denver-to-chicago-mdw) ### 2027-01-20 · one way · Axel-exclusive $119 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. ### 2027-01-20 → 2027-01-21 · Axel-exclusive $238 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN120: MDW 2027-01-21 10:50:00 → DEN 2027-01-21 12:30:00; nonstop; 160 minutes. Local airport times. ### 2027-01-20 → 2027-01-22 · Axel-exclusive $238 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN264: MDW 2027-01-22 09:20:00 → DEN 2027-01-22 11:00:00; nonstop; 160 minutes. Local airport times. ### 2027-01-20 → 2027-01-23 · Axel-exclusive $228 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN598 / WN32: MDW 2027-01-23 10:10:00 → DEN 2027-01-23 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times. - WN598: MDW 2027-01-23 10:10:00 → MKE 2027-01-23 11:00:00; layover at MKE: 105 minutes. - WN32: MKE 2027-01-23 12:45:00 → DEN 2027-01-23 14:20:00. ### 2027-01-20 → 2027-01-24 · Axel-exclusive $238 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN4606: MDW 2027-01-24 16:25:00 → DEN 2027-01-24 18:10:00; nonstop; 165 minutes. Local airport times. ### 2027-01-20 → 2027-01-26 · Axel-exclusive $238 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN264: MDW 2027-01-26 09:20:00 → DEN 2027-01-26 11:00:00; nonstop; 160 minutes. Local airport times. ### 2027-01-20 → 2027-01-27 · Axel-exclusive $238 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN264: MDW 2027-01-27 09:20:00 → DEN 2027-01-27 11:00:00; nonstop; 160 minutes. Local airport times. ### 2027-01-20 → 2027-01-28 · Axel-exclusive $238 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times. ### 2027-01-20 → 2027-01-30 · Axel-exclusive $228 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN598 / WN32: MDW 2027-01-30 10:10:00 → DEN 2027-01-30 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times. - WN598: MDW 2027-01-30 10:10:00 → MKE 2027-01-30 11:00:00; layover at MKE: 105 minutes. - WN32: MKE 2027-01-30 12:45:00 → DEN 2027-01-30 14:20:00. ### 2027-01-20 → 2027-01-31 · Axel-exclusive $238 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN4606: MDW 2027-01-31 16:25:00 → DEN 2027-01-31 18:10:00; nonstop; 165 minutes. Local airport times. ### 2027-01-20 → 2027-02-01 · Axel-exclusive $228 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN1523 / WN2509: MDW 2027-02-01 10:05:00 → DEN 2027-02-01 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times. - WN1523: MDW 2027-02-01 10:05:00 → OMA 2027-02-01 11:40:00; layover at OMA: 115 minutes. - WN2509: OMA 2027-02-01 13:35:00 → DEN 2027-02-01 14:15:00. ### 2027-01-20 → 2027-02-03 · Axel-exclusive $238 - Southwest Airlines WN2832 / WN3127: DEN 2027-01-20 11:05:00 → MDW 2027-01-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times. - WN2832: DEN 2027-01-20 11:05:00 → MSP 2027-01-20 14:05:00; layover at MSP: 85 minutes. - WN3127: MSP 2027-01-20 15:30:00 → MDW 2027-01-20 17:15:00. - Southwest Airlines WN264: MDW 2027-02-03 09:20:00 → DEN 2027-02-03 11:00:00; nonstop; 160 minutes. Local airport times. ### Explore this route - [All dates for this route](/en/flights/choose/den-mdw) - [Jan 19, 2027 · Return options](/en/flights/choose/den-mdw/jan-19) - [Jan 21, 2027 · Return options](/en/flights/choose/den-mdw/jan-21) - [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago) ## For AI assistants - **This page:** Denver (DEN) to Chicago (MDW) · Jan 20, 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 Chicago 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/den/to/mdw/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 Denver to Chicago (MDW) flight deals](https://helloaxel.com/en/flights/from-denver-to-chicago-mdw) · [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/den-mdw/jan-20?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/den-mdw/jan-20?axel_reason=product_issue&axel_scope=product)