Denver (DEN) to Chicago (MDW), Nov 25, 2026: round trips from $282, one way from $169

Denver (DEN) to Chicago (MDW), Nov 25, 2026: round trips from $282, one way from $169 on Axel, checked Nov 13, 2026. Lowest published fares: $282 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 25, 2026 – Dec 5, 2026; $169 one way, Axel-exclusive, Southwest Airlines, 1 stop, Nov 25, 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 25–26, 2026 · 1 night · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $99 a night · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $70 a night · 5★ Sofitel Chicago Magnificent Mile, $210 a night
• Hotels in Chicago for these nights (Nov 25–27, 2026 · 2 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $108 a night, $215 for 2 nights · 4★ Freehand Chicago, $78 a night, $155 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $205 a night, $409 for 2 nights
• Hotels in Chicago for these nights (Nov 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $131 a night, $392 for 3 nights · 4★ Freehand Chicago, $80 a night, $240 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $237 a night, $712 for 3 nights
• Hotels in Chicago for these nights (Nov 25–29, 2026 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $137 a night, $548 for 4 nights · 4★ Freehand Chicago, $81 a night, $325 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $252 a night, $1,009 for 4 nights
• Hotels in Chicago for these nights (Nov 25–30, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $132 a night, $662 for 5 nights · 4★ Freehand Chicago, $82 a night, $410 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $264 a night, $1,318 for 5 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 1, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $129 a night, $776 for 6 nights · 4★ Freehand Chicago, $82 a night, $494 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $273 a night, $1,635 for 6 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 2, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $131 a night, $916 for 7 nights · 4★ Freehand Chicago, $83 a night, $578 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $278 a night, $1,944 for 7 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 3, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $129 a night, $1,035 for 8 nights · 4★ Freehand Chicago, $83 a night, $662 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $280 a night, $2,241 for 8 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 4, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $128 a night, $1,154 for 9 nights · 4★ Freehand Chicago, $82 a night, $741 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $275 a night, $2,475 for 9 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 5, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $131 a night, $1,309 for 10 nights · 4★ Freehand Chicago, $83 a night, $825 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $277 a night, $2,772 for 10 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 6, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $134 a night, $1,475 for 11 nights · 4★ Freehand Chicago, $83 a night, $908 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $280 a night, $3,081 for 11 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 7, 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, $81 a night, $971 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $274 a night, $3,287 for 12 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 8, 2026 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $129 a night, $1,683 for 13 nights · 4★ Freehand Chicago, $80 a night, $1,043 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $269 a night, $3,501 for 13 nights
• Hotels in Chicago for these nights (Nov 25 – Dec 9, 2026 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $130 a night, $1,817 for 14 nights · 4★ Freehand Chicago, $80 a night, $1,115 for 14 nights · 5★ Nobu Hotel Chicago, $508 a night, $7,115 for 14 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2026-11-25 · one way · Axel-exclusive $169

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.

2026-11-25 → 2026-11-26 · Axel-exclusive $338

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• Southwest Airlines WN120: MDW 2026-11-26 10:50:00 → DEN 2026-11-26 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-25 → 2026-11-27 · Axel-exclusive $338

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-25 → 2026-11-28 · Axel-exclusive $324

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• 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.

2026-11-25 → 2026-11-29 · Axel-exclusive $338

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• Southwest Airlines WN4606: MDW 2026-11-29 16:25:00 → DEN 2026-11-29 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $292

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• Southwest Airlines WN120: MDW 2026-12-01 10:50:00 → DEN 2026-12-01 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $292

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• Southwest Airlines WN120: MDW 2026-12-02 10:50:00 → DEN 2026-12-02 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-25 → 2026-12-03 · Axel-exclusive $292

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• Southwest Airlines WN120: MDW 2026-12-03 10:50:00 → DEN 2026-12-03 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $282

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• 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.

2026-11-25 → 2026-12-06 · Axel-exclusive $292

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• Southwest Airlines WN4606: MDW 2026-12-06 16:25:00 → DEN 2026-12-06 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-25 → 2026-12-07 · Axel-exclusive $282

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• 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.

2026-11-25 → 2026-12-09 · Axel-exclusive $292

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-25 11:05:00 → MDW 2026-11-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-25 11:05:00 → MSP 2026-11-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-25 15:30:00 → MDW 2026-11-25 17:15:00.
• Southwest Airlines WN2931: MDW 2026-12-09 17:05:00 → DEN 2026-12-09 18:50:00; nonstop; 165 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 24, 2026 · Return options
• Nov 26, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Nov 25, 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.
• 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 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 · Flight search guide.
• 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.

Feedback (optional): Missing info · Axel issue