Denver (DEN) to Chicago (MDW), Nov 19, 2026: round trips from $260, one way from $135

Denver (DEN) to Chicago (MDW), Nov 19, 2026: round trips from $260, one way from $135 on Axel, checked Nov 13, 2026. Lowest published fares: $260 round trip, Axel-exclusive, Southwest Airlines, nonstop, Nov 19, 2026 – Dec 1, 2026; $135 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 19, 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 19–20, 2026 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $108 a night · 4★ Freehand Chicago, $86 a night · 5★ Sofitel Chicago Magnificent Mile, $314 a night
• Hotels in Chicago for these nights (Nov 19–21, 2026 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $157 a night, $314 for 2 nights · 4★ Freehand Chicago, $87 a night, $173 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $306 a night, $611 for 2 nights
• Hotels in Chicago for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $171 a night, $512 for 3 nights · 4★ Freehand Chicago, $86 a night, $258 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $288 a night, $864.50 for 3 nights
• Hotels in Chicago for these nights (Nov 19–23, 2026 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $155 a night, $621 for 4 nights · 4★ Freehand Chicago, $86 a night, $345 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $269 a night, $1,074.50 for 4 nights
• Hotels in Chicago for these nights (Nov 19–24, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $146 a night, $730 for 5 nights · 4★ Freehand Chicago, $86 a night, $430 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $257 a night, $1,284.50 for 5 nights
• Hotels in Chicago for these nights (Nov 19–25, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $140 a night, $839 for 6 nights · 4★ Freehand Chicago, $84 a night, $502 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $248 a night, $1,487.50 for 6 nights
• Hotels in Chicago for these nights (Nov 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $134 a night, $940 for 7 nights · 4★ Freehand Chicago, $82 a night, $573 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $243 a night, $1,697.50 for 7 nights
• Hotels in Chicago for these nights (Nov 19–27, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $135 a night, $1,077 for 8 nights · 4★ Freehand Chicago, $82 a night, $657 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $237 a night, $1,896.50 for 8 nights
• Hotels in Chicago for these nights (Nov 19–28, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $138 a night, $1,244 for 9 nights · 4★ Freehand Chicago, $82 a night, $742 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $244 a night, $2,199.50 for 9 nights
• Hotels in Chicago for these nights (Nov 19–29, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $139 a night, $1,387 for 10 nights · 4★ Freehand Chicago, $83 a night, $827 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $250 a night, $2,496.50 for 10 nights
• Hotels in Chicago for these nights (Nov 19–30, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $136 a night, $1,501 for 11 nights · 4★ Freehand Chicago, $83 a night, $912 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $255 a night, $2,805.50 for 11 nights
• Hotels in Chicago for these nights (Nov 19 – Dec 1, 2026 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $135 a night, $1,615 for 12 nights · 4★ Freehand Chicago, $83 a night, $996 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $260 a night, $3,122.50 for 12 nights
• Hotels in Chicago for these nights (Nov 19 – Dec 2, 2026 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $135 a night, $1,755 for 13 nights · 4★ Freehand Chicago, $83 a night, $1,080 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $264 a night, $3,431.50 for 13 nights
• Hotels in Chicago for these nights (Nov 19 – Dec 3, 2026 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $134 a night, $1,874 for 14 nights · 4★ Freehand Chicago, $83 a night, $1,164 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $266 a night, $3,728.50 for 14 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2026-11-19 · one way · Axel-exclusive $135

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; nonstop; 140 minutes. Local airport times.

2026-11-19 → 2026-11-20 · Axel-exclusive $306

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2602: MDW 2026-11-20 08:05:00 → DEN 2026-11-20 10:00:00; nonstop; 175 minutes. Local airport times.

2026-11-19 → 2026-11-21 · Axel-exclusive $292

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

2026-11-19 → 2026-11-22 · Axel-exclusive $306

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

2026-11-19 → 2026-11-23 · Axel-exclusive $292

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

2026-11-19 → 2026-11-25 · Axel-exclusive $306

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; nonstop; 140 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.

2026-11-19 → 2026-11-26 · Axel-exclusive $306

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

2026-11-19 → 2026-11-27 · Axel-exclusive $306

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

2026-11-19 → 2026-11-29 · Axel-exclusive $306

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

2026-11-19 → 2026-11-30 · Axel-exclusive $292

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

2026-11-19 → 2026-12-01 · Axel-exclusive $260

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

2026-11-19 → 2026-12-03 · Axel-exclusive $260

• Southwest Airlines WN1698: DEN 2026-11-19 14:05:00 → MDW 2026-11-19 17:25:00; 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.

Explore this route

• All dates for this route
• Nov 18, 2026 · Return options
• Nov 20, 2026 · Return options
• Hotels in Chicago with Axel

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• This page: Denver (DEN) to Chicago (MDW) · Nov 19, 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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