Denver (DEN) to Chicago (MDW), Nov 21, 2026: round trips from $296, one way from $182

Denver (DEN) to Chicago (MDW), Nov 21, 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 21, 2026 – Dec 5, 2026; $182 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 21, 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 21–22, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $187 a night · 4★ Freehand Chicago, $85 a night · 5★ Sofitel Chicago Magnificent Mile, $253.50 a night
• Hotels in Chicago for these nights (Nov 21–23, 2026 · 2 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $153 a night, $305 for 2 nights · 4★ Freehand Chicago, $86 a night, $172 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $232 a night, $463.50 for 2 nights
• Hotels in Chicago for these nights (Nov 21–24, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $139 a night, $416 for 3 nights · 4★ Freehand Chicago, $86 a night, $257 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $225 a night, $673.50 for 3 nights
• Hotels in Chicago for these nights (Nov 21–25, 2026 · 4 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $128 a night, $512 for 4 nights · 4★ Freehand Chicago, $82 a night, $329 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $219 a night, $876.50 for 4 nights
• Hotels in Chicago for these nights (Nov 21–26, 2026 · 5 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $122 a night, $611 for 5 nights · 4★ Freehand Chicago, $80 a night, $400 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $217 a night, $1,086.50 for 5 nights
• Hotels in Chicago for these nights (Nov 21–27, 2026 · 6 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $121 a night, $727 for 6 nights · 4★ Freehand Chicago, $81 a night, $484 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $214 a night, $1,285.50 for 6 nights
• Hotels in Chicago for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $129 a night, $904 for 7 nights · 4★ Freehand Chicago, $81 a night, $569 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $227 a night, $1,588.50 for 7 nights
• Hotels in Chicago for these nights (Nov 21–29, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $134 a night, $1,073 for 8 nights · 4★ Freehand Chicago, $82 a night, $654 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $236 a night, $1,885.50 for 8 nights
• Hotels in Chicago for these nights (Nov 21–30, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $132 a night, $1,187 for 9 nights · 4★ Freehand Chicago, $82 a night, $739 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $244 a night, $2,194.50 for 9 nights
• Hotels in Chicago for these nights (Nov 21 – Dec 1, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $130 a night, $1,301 for 10 nights · 4★ Freehand Chicago, $82 a night, $823 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $251 a night, $2,511.50 for 10 nights
• Hotels in Chicago for these nights (Nov 21 – Dec 2, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $131 a night, $1,441 for 11 nights · 4★ Freehand Chicago, $82 a night, $907 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $256 a night, $2,820.50 for 11 nights
• Hotels in Chicago for these nights (Nov 21 – Dec 3, 2026 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $130 a night, $1,560 for 12 nights · 4★ Freehand Chicago, $83 a night, $991 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $260 a night, $3,117.50 for 12 nights
• Hotels in Chicago for these nights (Nov 21 – Dec 4, 2026 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $129 a night, $1,679 for 13 nights · 4★ Freehand Chicago, $82 a night, $1,070 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $258 a night, $3,351.50 for 13 nights
• Hotels in Chicago for these nights (Nov 21 – Dec 5, 2026 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $131 a night, $1,834 for 14 nights · 4★ Freehand Chicago, $82 a night, $1,154 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

2026-11-21 · one way · Axel-exclusive $182

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 minutes. Local airport times.

2026-11-21 → 2026-11-22 · Axel-exclusive $351

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-11-23 · Axel-exclusive $338

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-11-24 · Axel-exclusive $351

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-11-25 · Axel-exclusive $351

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2026-11-25 16:25:00 → DEN 2026-11-25 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-21 → 2026-11-27 · Axel-exclusive $351

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-11-28 · Axel-exclusive $338

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-11-29 · Axel-exclusive $351

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-12-01 · Axel-exclusive $306

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-12-02 · Axel-exclusive $306

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-12-03 · Axel-exclusive $306

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

2026-11-21 → 2026-12-05 · Axel-exclusive $296

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 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.

Explore this route

• All dates for this route
• Nov 20, 2026 · Return options
• Nov 22, 2026 · Return options
• Hotels in Chicago with Axel

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• This page: Denver (DEN) to Chicago (MDW) · Nov 21, 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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