Denver (DEN) to Chicago (MDW), Nov 20, 2026: round trips from $306, one way from $182

Denver (DEN) to Chicago (MDW), Nov 20, 2026: round trips from $306, one way from $182 on Axel, checked Nov 13, 2026. Lowest published fares: $306 round trip, Axel-exclusive, Southwest Airlines, nonstop, Nov 20, 2026 – Dec 1, 2026; $182 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 20, 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 20–21, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $182 a night · 4★ Freehand Chicago, $87 a night · 5★ Sofitel Chicago Magnificent Mile, $297 a night
• Hotels in Chicago for these nights (Nov 20–22, 2026 · 2 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $185 a night, $369 for 2 nights · 4★ Freehand Chicago, $86 a night, $172 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $275 a night, $550.50 for 2 nights
• Hotels in Chicago for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $162 a night, $487 for 3 nights · 4★ Freehand Chicago, $86 a night, $259 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $254 a night, $760.50 for 3 nights
• Hotels in Chicago for these nights (Nov 20–24, 2026 · 4 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $151 a night, $605 for 4 nights · 4★ Freehand Chicago, $86 a night, $344 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $243 a night, $970.50 for 4 nights
• Hotels in Chicago for these nights (Nov 20–25, 2026 · 5 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $141 a night, $707 for 5 nights · 4★ Freehand Chicago, $83 a night, $416 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $235 a night, $1,173.50 for 5 nights
• Hotels in Chicago for these nights (Nov 20–26, 2026 · 6 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $134 a night, $806 for 6 nights · 4★ Freehand Chicago, $81 a night, $487 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $231 a night, $1,383.50 for 6 nights
• Hotels in Chicago for these nights (Nov 20–27, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $132 a night, $922 for 7 nights · 4★ Freehand Chicago, $82 a night, $571 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $226 a night, $1,582.50 for 7 nights
• Hotels in Chicago for these nights (Nov 20–28, 2026 · 8 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $137 a night, $1,099 for 8 nights · 4★ Freehand Chicago, $82 a night, $656 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $236 a night, $1,885.50 for 8 nights
• Hotels in Chicago for these nights (Nov 20–29, 2026 · 9 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $142 a night, $1,275 for 9 nights · 4★ Freehand Chicago, $82 a night, $741 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $243 a night, $2,182.50 for 9 nights
• Hotels in Chicago for these nights (Nov 20–30, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $139 a night, $1,393 for 10 nights · 4★ Freehand Chicago, $83 a night, $826 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $249 a night, $2,491.50 for 10 nights
• Hotels in Chicago for these nights (Nov 20 – Dec 1, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $137 a night, $1,507 for 11 nights · 4★ Freehand Chicago, $83 a night, $910 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $255 a night, $2,808.50 for 11 nights
• Hotels in Chicago for these nights (Nov 20 – Dec 2, 2026 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $137 a night, $1,647 for 12 nights · 4★ Freehand Chicago, $83 a night, $994 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $260 a night, $3,117.50 for 12 nights
• Hotels in Chicago for these nights (Nov 20 – Dec 3, 2026 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $136 a night, $1,766 for 13 nights · 4★ Freehand Chicago, $83 a night, $1,078 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $263 a night, $3,414.50 for 13 nights
• Hotels in Chicago for these nights (Nov 20 – Dec 4, 2026 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $135 a night, $1,885 for 14 nights · 4★ Freehand Chicago, $83 a night, $1,157 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $261 a night, $3,648.50 for 14 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2026-11-20 · one way · Axel-exclusive $182

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.

2026-11-20 → 2026-11-21 · Axel-exclusive $338

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

2026-11-20 → 2026-11-22 · Axel-exclusive $351

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2026-11-22 16:25:00 → DEN 2026-11-22 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-20 → 2026-11-23 · Axel-exclusive $338

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN3051 / WN2162: MDW 2026-11-23 09:50:00 → DEN 2026-11-23 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-11-23 09:50:00 → TUL 2026-11-23 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-11-23 12:55:00 → DEN 2026-11-23 13:45:00.

2026-11-20 → 2026-11-24 · Axel-exclusive $351

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2602: MDW 2026-11-24 08:05:00 → DEN 2026-11-24 10:00:00; nonstop; 175 minutes. Local airport times.

2026-11-20 → 2026-11-26 · Axel-exclusive $351

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2026-11-26 10:50:00 → DEN 2026-11-26 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-20 → 2026-11-27 · Axel-exclusive $351

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-20 → 2026-11-28 · Axel-exclusive $338

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 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.

2026-11-20 → 2026-11-30 · Axel-exclusive $338

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 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.

2026-11-20 → 2026-12-01 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 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.

2026-11-20 → 2026-12-02 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2026-12-02 10:50:00 → DEN 2026-12-02 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-20 → 2026-12-04 · Axel-exclusive $306

• Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 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.

Explore this route

• All dates for this route
• Nov 19, 2026 · Return options
• Nov 21, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Nov 20, 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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