Denver (DEN) to Chicago (MDW), Jan 25, 2027: round trips from $228, one way from $119

Denver (DEN) to Chicago (MDW), Jan 25, 2027: round trips from $228, one way from $119 on Axel, checked Nov 13, 2026. Lowest published fares: $228 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 25–30, 2027; $119 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 25, 2027; 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 (Jan 25–26, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 a night · 4★ Freehand Chicago, $73 a night · 5★ Waldorf Astoria Chicago, $413 a night
• Hotels in Chicago for these nights (Jan 25–27, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $158 for 2 nights · 4★ Freehand Chicago, $73 a night, $146 for 2 nights · 5★ Waldorf Astoria Chicago, $409 a night, $818 for 2 nights
• Hotels in Chicago for these nights (Jan 25–28, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $233 for 3 nights · 4★ Freehand Chicago, $73 a night, $218 for 3 nights · 5★ Waldorf Astoria Chicago, $410 a night, $1,231 for 3 nights
• Hotels in Chicago for these nights (Jan 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $77 a night, $308 for 4 nights · 4★ Freehand Chicago, $73 a night, $290 for 4 nights · 5★ Nobu Hotel Chicago, $405 a night, $1,620 for 4 nights
• Hotels in Chicago for these nights (Jan 25–30, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $392 for 5 nights · 4★ Freehand Chicago, $74 a night, $369 for 5 nights · 5★ Nobu Hotel Chicago, $401 a night, $2,007 for 5 nights
• Hotels in Chicago for these nights (Jan 25–31, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $467 for 6 nights · 4★ Freehand Chicago, $75 a night, $447 for 6 nights · 5★ Nobu Hotel Chicago, $397 a night, $2,383 for 6 nights
• Hotels in Chicago for these nights (Jan 25 – Feb 1, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $550 for 7 nights · 4★ Freehand Chicago, $74 a night, $519 for 7 nights · 5★ Nobu Hotel Chicago, $390 a night, $2,732 for 7 nights
• Hotels in Chicago for these nights (Jan 25 – Feb 2, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $80 a night, $639 for 8 nights · 4★ Freehand Chicago, $74 a night, $592 for 8 nights · 5★ Nobu Hotel Chicago, $389 a night, $3,110 for 8 nights
• Hotels in Chicago for these nights (Jan 25 – Feb 3, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $81 a night, $728 for 9 nights · 4★ Freehand Chicago, $74 a night, $663 for 9 nights · 5★ Nobu Hotel Chicago, $391 a night, $3,523 for 9 nights
• Hotels in Chicago for these nights (Jan 25 – Feb 4, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $82 a night, $817 for 10 nights · 4★ Freehand Chicago, $74 a night, $736 for 10 nights · 5★ Nobu Hotel Chicago, $391 a night, $3,914 for 10 nights
• Hotels in Chicago for these nights (Jan 25 – Feb 5, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $83 a night, $916 for 11 nights · 4★ Freehand Chicago, $73 a night, $808 for 11 nights · 5★ Nobu Hotel Chicago, $391 a night, $4,296 for 11 nights
• Hotels in Chicago for these nights (Jan 25 – Feb 6, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $84 a night, $1,005 for 12 nights · 4★ Freehand Chicago, $74 a night, $887 for 12 nights · 5★ Nobu Hotel Chicago, $391 a night, $4,687 for 12 nights
• Hotels in Chicago for these nights (Jan 25 – Feb 7, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $84 a night, $1,094 for 13 nights · 4★ Freehand Chicago, $74 a night, $966 for 13 nights · 5★ Nobu Hotel Chicago, $391 a night, $5,078 for 13 nights
• Hotels in Chicago for these nights (Jan 25 – Feb 8, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $85 a night, $1,193 for 14 nights · 4★ Freehand Chicago, $74 a night, $1,039 for 14 nights · 5★ Nobu Hotel Chicago, $388 a night, $5,427 for 14 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2027-01-25 · one way · Axel-exclusive $119

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.

2027-01-25 → 2027-01-26 · Axel-exclusive $238

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN264: MDW 2027-01-26 09:20:00 → DEN 2027-01-26 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-27 · Axel-exclusive $238

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN264: MDW 2027-01-27 09:20:00 → DEN 2027-01-27 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-28 · Axel-exclusive $238

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-29 · Axel-exclusive $238

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN264: MDW 2027-01-29 09:20:00 → DEN 2027-01-29 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-31 · Axel-exclusive $238

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN4606: MDW 2027-01-31 16:25:00 → DEN 2027-01-31 18:10:00; nonstop; 165 minutes. Local airport times.

2027-01-25 → 2027-02-01 · Axel-exclusive $228

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN1523 / WN2509: MDW 2027-02-01 10:05:00 → DEN 2027-02-01 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-02-01 10:05:00 → OMA 2027-02-01 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-02-01 13:35:00 → DEN 2027-02-01 14:15:00.

2027-01-25 → 2027-02-02 · Axel-exclusive $238

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN264: MDW 2027-02-02 09:20:00 → DEN 2027-02-02 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-02-04 · Axel-exclusive $238

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN120: MDW 2027-02-04 10:50:00 → DEN 2027-02-04 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-02-05 · Axel-exclusive $238

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN264: MDW 2027-02-05 09:20:00 → DEN 2027-02-05 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-02-06 · Axel-exclusive $228

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN598 / WN32: MDW 2027-02-06 10:10:00 → DEN 2027-02-06 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
  • WN598: MDW 2027-02-06 10:10:00 → MKE 2027-02-06 11:00:00; layover at MKE: 105 minutes.
  • WN32: MKE 2027-02-06 12:45:00 → DEN 2027-02-06 14:20:00.

2027-01-25 → 2027-02-08 · Axel-exclusive $228

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-25 11:05:00 → MDW 2027-01-25 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-25 11:05:00 → MSP 2027-01-25 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-25 15:30:00 → MDW 2027-01-25 17:15:00.
• Southwest Airlines WN1523 / WN2509: MDW 2027-02-08 10:05:00 → DEN 2027-02-08 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-02-08 10:05:00 → OMA 2027-02-08 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-02-08 13:35:00 → DEN 2027-02-08 14:15:00.

Explore this route

• All dates for this route
• Jan 24, 2027 · Return options
• Jan 26, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Jan 25, 2027 · 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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