Denver (DEN) to Chicago (MDW), Jan 24, 2027: round trips from $238, one way from $128

Denver (DEN) to Chicago (MDW), Jan 24, 2027: round trips from $238, one way from $128 on Axel, checked Nov 13, 2026. Lowest published fares: $238 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 24–25, 2027; $128 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 24, 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 24–25, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 a night · 4★ Freehand Chicago, $71 a night · 5★ Nobu Hotel Chicago, $349 a night
• Hotels in Chicago for these nights (Jan 24–26, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $158 for 2 nights · 4★ Freehand Chicago, $72 a night, $144 for 2 nights · 5★ Nobu Hotel Chicago, $391 a night, $782 for 2 nights
• Hotels in Chicago for these nights (Jan 24–27, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $80 a night, $241 for 3 nights · 4★ Freehand Chicago, $72 a night, $217 for 3 nights · 5★ Nobu Hotel Chicago, $403 a night, $1,210 for 3 nights
• Hotels in Chicago for these nights (Jan 24–28, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $316 for 4 nights · 4★ Freehand Chicago, $72 a night, $289 for 4 nights · 5★ Nobu Hotel Chicago, $399 a night, $1,597 for 4 nights
• Hotels in Chicago for these nights (Jan 24–29, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $391 for 5 nights · 4★ Freehand Chicago, $72 a night, $361 for 5 nights · 5★ Nobu Hotel Chicago, $394 a night, $1,969 for 5 nights
• Hotels in Chicago for these nights (Jan 24–30, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $475 for 6 nights · 4★ Freehand Chicago, $73 a night, $440 for 6 nights · 5★ Nobu Hotel Chicago, $393 a night, $2,356 for 6 nights
• Hotels in Chicago for these nights (Jan 24–31, 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, $518 for 7 nights · 5★ Nobu Hotel Chicago, $390 a night, $2,732 for 7 nights
• Hotels in Chicago for these nights (Jan 24 – Feb 1, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $633 for 8 nights · 4★ Freehand Chicago, $74 a night, $590 for 8 nights · 5★ Nobu Hotel Chicago, $385 a night, $3,081 for 8 nights
• Hotels in Chicago for these nights (Jan 24 – Feb 2, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $80 a night, $722 for 9 nights · 4★ Freehand Chicago, $74 a night, $663 for 9 nights · 5★ Nobu Hotel Chicago, $384 a night, $3,459 for 9 nights
• Hotels in Chicago for these nights (Jan 24 – Feb 3, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $81 a night, $811 for 10 nights · 4★ Freehand Chicago, $73 a night, $734 for 10 nights · 5★ Nobu Hotel Chicago, $387 a night, $3,872 for 10 nights
• Hotels in Chicago for these nights (Jan 24 – Feb 4, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $82 a night, $900 for 11 nights · 4★ Freehand Chicago, $73 a night, $807 for 11 nights · 5★ Nobu Hotel Chicago, $388 a night, $4,263 for 11 nights
• Hotels in Chicago for these nights (Jan 24 – Feb 5, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $83 a night, $999 for 12 nights · 4★ Freehand Chicago, $73 a night, $879 for 12 nights · 5★ Nobu Hotel Chicago, $387 a night, $4,645 for 12 nights
• Hotels in Chicago for these nights (Jan 24 – Feb 6, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $84 a night, $1,088 for 13 nights · 4★ Freehand Chicago, $74 a night, $958 for 13 nights · 5★ Nobu Hotel Chicago, $387 a night, $5,036 for 13 nights
• Hotels in Chicago for these nights (Jan 24 – Feb 7, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $84 a night, $1,177 for 14 nights · 4★ Freehand Chicago, $74 a night, $1,037 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

2027-01-24 · one way · Axel-exclusive $128

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.

2027-01-24 → 2027-01-25 · Axel-exclusive $238

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-25 10:05:00 → DEN 2027-01-25 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-25 10:05:00 → OMA 2027-01-25 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-25 13:35:00 → DEN 2027-01-25 14:15:00.

2027-01-24 → 2027-01-26 · Axel-exclusive $247

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-26 09:20:00 → DEN 2027-01-26 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-24 → 2027-01-27 · Axel-exclusive $247

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-27 09:20:00 → DEN 2027-01-27 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-24 → 2027-01-28 · Axel-exclusive $247

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-24 → 2027-01-30 · Axel-exclusive $238

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN598 / WN32: MDW 2027-01-30 10:10:00 → DEN 2027-01-30 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
  • WN598: MDW 2027-01-30 10:10:00 → MKE 2027-01-30 11:00:00; layover at MKE: 105 minutes.
  • WN32: MKE 2027-01-30 12:45:00 → DEN 2027-01-30 14:20:00.

2027-01-24 → 2027-01-31 · Axel-exclusive $247

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2027-01-31 16:25:00 → DEN 2027-01-31 18:10:00; nonstop; 165 minutes. Local airport times.

2027-01-24 → 2027-02-01 · Axel-exclusive $238

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• 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.

2027-01-24 → 2027-02-03 · Axel-exclusive $247

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-02-03 09:20:00 → DEN 2027-02-03 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-24 → 2027-02-04 · Axel-exclusive $247

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2027-02-04 10:50:00 → DEN 2027-02-04 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-24 → 2027-02-05 · Axel-exclusive $247

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-02-05 09:20:00 → DEN 2027-02-05 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-24 → 2027-02-07 · Axel-exclusive $247

• Southwest Airlines WN1699: DEN 2027-01-24 17:35:00 → MDW 2027-01-24 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2027-02-07 16:25:00 → DEN 2027-02-07 18:10:00; nonstop; 165 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 23, 2027 · Return options
• Jan 25, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Jan 24, 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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