Denver (DEN) to Chicago (MDW), Nov 27, 2026: round trips from $296, one way from $182

Denver (DEN) to Chicago (MDW), Nov 27, 2026: round trips from $296, one way from $182 on Axel, checked Nov 13, 2026. Lowest published fares: $296 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 27, 2026 – Dec 5, 2026; $182 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 27, 2026; 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.

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 (Nov 27–28, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $164 a night · 4★ Freehand Chicago, $85 a night · 5★ Sofitel Chicago Magnificent Mile, $303 a night
• Hotels in Chicago for these nights (Nov 27–29, 2026 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $155 a night, $310 for 2 nights · 4★ Freehand Chicago, $85 a night, $170 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $300 a night, $600 for 2 nights
• Hotels in Chicago for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $141 a night, $424 for 3 nights · 4★ Freehand Chicago, $85 a night, $255 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $303 a night, $909 for 3 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 1, 2026 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $135 a night, $538 for 4 nights · 4★ Freehand Chicago, $85 a night, $339 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $307 a night, $1,226 for 4 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 2, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $136 a night, $678 for 5 nights · 4★ Freehand Chicago, $85 a night, $423 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $307 a night, $1,535 for 5 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 3, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $133 a night, $797 for 6 nights · 4★ Freehand Chicago, $85 a night, $507 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $305 a night, $1,832 for 6 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 4, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $130 a night, $911 for 7 nights · 4★ Freehand Chicago, $84 a night, $586 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $295 a night, $2,066 for 7 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 5, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $134 a night, $1,071 for 8 nights · 4★ Freehand Chicago, $84 a night, $670 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $295 a night, $2,363 for 8 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 6, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $137 a night, $1,237 for 9 nights · 4★ Freehand Chicago, $84 a night, $753 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $297 a night, $2,672 for 9 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 7, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $134 a night, $1,341 for 10 nights · 4★ Freehand Chicago, $82 a night, $816 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $288 a night, $2,878 for 10 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 8, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $131 a night, $1,445 for 11 nights · 4★ Freehand Chicago, $81 a night, $888 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $281 a night, $3,092 for 11 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 9, 2026 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $132 a night, $1,579 for 12 nights · 4★ Freehand Chicago, $80 a night, $960 for 12 nights · 5★ Nobu Hotel Chicago, $530 a night, $6,354 for 12 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 10, 2026 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $129 a night, $1,677 for 13 nights · 4★ Freehand Chicago, $79 a night, $1,032 for 13 nights · 5★ Nobu Hotel Chicago, $539 a night, $7,008 for 13 nights
• Hotels in Chicago for these nights (Nov 27 – Dec 11, 2026 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $127 a night, $1,775 for 14 nights · 4★ Freehand Chicago, $79 a night, $1,104 for 14 nights · 5★ Waldorf Astoria Chicago, $539 a night, $7,546 for 14 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2026-11-27 · one way · Axel-exclusive $182

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.

2026-11-27 → 2026-11-28 · Axel-exclusive $338

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN1742 / WN2668: MDW 2026-11-28 17:10:00 → DEN 2026-11-28 21:45:00; 1 stop(s) via MCI; 335 minutes. Local airport times.
  • WN1742: MDW 2026-11-28 17:10:00 → MCI 2026-11-28 18:40:00; layover at MCI: 135 minutes.
  • WN2668: MCI 2026-11-28 20:55:00 → DEN 2026-11-28 21:45:00.

2026-11-27 → 2026-11-29 · Axel-exclusive $351

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2026-11-29 16:25:00 → DEN 2026-11-29 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-27 → 2026-11-30 · Axel-exclusive $338

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN3051 / WN2162: MDW 2026-11-30 09:50:00 → DEN 2026-11-30 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-11-30 09:50:00 → TUL 2026-11-30 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-11-30 12:55:00 → DEN 2026-11-30 13:45:00.

2026-11-27 → 2026-12-01 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2026-12-01 10:50:00 → DEN 2026-12-01 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2026-12-03 10:50:00 → DEN 2026-12-03 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-27 → 2026-12-05 · Axel-exclusive $296

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN598 / WN32: MDW 2026-12-05 10:10:00 → DEN 2026-12-05 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
  • WN598: MDW 2026-12-05 10:10:00 → MKE 2026-12-05 11:00:00; layover at MKE: 105 minutes.
  • WN32: MKE 2026-12-05 12:45:00 → DEN 2026-12-05 14:20:00.

2026-11-27 → 2026-12-07 · Axel-exclusive $296

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN1523 / WN2509: MDW 2026-12-07 10:05:00 → DEN 2026-12-07 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2026-12-07 10:05:00 → OMA 2026-12-07 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2026-12-07 13:35:00 → DEN 2026-12-07 14:15:00.

2026-11-27 → 2026-12-08 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2931: MDW 2026-12-08 17:05:00 → DEN 2026-12-08 18:50:00; nonstop; 165 minutes. Local airport times.

2026-11-27 → 2026-12-09 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2931: MDW 2026-12-09 17:05:00 → DEN 2026-12-09 18:50:00; nonstop; 165 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2931: MDW 2026-12-11 17:05:00 → DEN 2026-12-11 18:50:00; nonstop; 165 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 26, 2026 · Return options
• Nov 28, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Nov 27, 2026 · 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.
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