Denver (DEN) to Chicago (MDW), Jan 15, 2027: round trips from $238, one way from $128

Denver (DEN) to Chicago (MDW), Jan 15, 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 15–16, 2027; $128 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 15, 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 15–16, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $83 a night · 4★ Freehand Chicago, $78 a night · 5★ Sofitel Chicago Magnificent Mile, $215 a night
• Hotels in Chicago for these nights (Jan 15–17, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $158 for 2 nights · 4★ Freehand Chicago, $79 a night, $157 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $217 a night, $434 for 2 nights
• Hotels in Chicago for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $233 for 3 nights · 4★ Freehand Chicago, $76 a night, $229 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $219 a night, $657 for 3 nights
• Hotels in Chicago for these nights (Jan 15–19, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $77 a night, $308 for 4 nights · 4★ Freehand Chicago, $75 a night, $301 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $228 a night, $911 for 4 nights
• Hotels in Chicago for these nights (Jan 15–20, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $77 a night, $383 for 5 nights · 4★ Freehand Chicago, $75 a night, $374 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $233 a night, $1,164 for 5 nights
• Hotels in Chicago for these nights (Jan 15–21, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $468 for 6 nights · 4★ Freehand Chicago, $74 a night, $446 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $229 a night, $1,374 for 6 nights
• Hotels in Chicago for these nights (Jan 15–22, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $551 for 7 nights · 4★ Freehand Chicago, $74 a night, $518 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $230 a night, $1,610 for 7 nights
• Hotels in Chicago for these nights (Jan 15–23, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $626 for 8 nights · 4★ Freehand Chicago, $75 a night, $596 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $228 a night, $1,820 for 8 nights
• Hotels in Chicago for these nights (Jan 15–24, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $701 for 9 nights · 4★ Freehand Chicago, $75 a night, $675 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $267 a night, $2,407 for 9 nights
• Hotels in Chicago for these nights (Jan 15–25, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $784 for 10 nights · 4★ Freehand Chicago, $75 a night, $746 for 10 nights · 5★ Nobu Hotel Chicago, $396 a night, $3,964 for 10 nights
• Hotels in Chicago for these nights (Jan 15–26, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $859 for 11 nights · 4★ Freehand Chicago, $74 a night, $819 for 11 nights · 5★ Nobu Hotel Chicago, $400 a night, $4,397 for 11 nights
• Hotels in Chicago for these nights (Jan 15–27, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $942 for 12 nights · 4★ Freehand Chicago, $74 a night, $892 for 12 nights · 5★ Nobu Hotel Chicago, $402 a night, $4,825 for 12 nights
• Hotels in Chicago for these nights (Jan 15–28, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $1,017 for 13 nights · 4★ Freehand Chicago, $74 a night, $964 for 13 nights · 5★ Nobu Hotel Chicago, $401 a night, $5,212 for 13 nights
• Hotels in Chicago for these nights (Jan 15–29, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $1,092 for 14 nights · 4★ Freehand Chicago, $74 a night, $1,036 for 14 nights · 5★ Nobu Hotel Chicago, $399 a night, $5,584 for 14 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2027-01-15 · one way · Axel-exclusive $128

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.

2027-01-15 → 2027-01-16 · Axel-exclusive $238

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN598 / WN32: MDW 2027-01-16 10:10:00 → DEN 2027-01-16 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
  • WN598: MDW 2027-01-16 10:10:00 → MKE 2027-01-16 11:00:00; layover at MKE: 105 minutes.
  • WN32: MKE 2027-01-16 12:45:00 → DEN 2027-01-16 14:20:00.

2027-01-15 → 2027-01-17 · Axel-exclusive $247

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2027-01-17 16:25:00 → DEN 2027-01-17 18:10:00; nonstop; 165 minutes. Local airport times.

2027-01-15 → 2027-01-18 · Axel-exclusive $238

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-18 10:05:00 → DEN 2027-01-18 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-18 10:05:00 → OMA 2027-01-18 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-18 13:35:00 → DEN 2027-01-18 14:15:00.

2027-01-15 → 2027-01-19 · Axel-exclusive $247

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-19 09:20:00 → DEN 2027-01-19 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-15 → 2027-01-21 · Axel-exclusive $247

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2027-01-21 10:50:00 → DEN 2027-01-21 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-15 → 2027-01-22 · Axel-exclusive $247

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-22 09:20:00 → DEN 2027-01-22 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-15 → 2027-01-23 · Axel-exclusive $238

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN598 / WN32: MDW 2027-01-23 10:10:00 → DEN 2027-01-23 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
  • WN598: MDW 2027-01-23 10:10:00 → MKE 2027-01-23 11:00:00; layover at MKE: 105 minutes.
  • WN32: MKE 2027-01-23 12:45:00 → DEN 2027-01-23 14:20:00.

2027-01-15 → 2027-01-25 · Axel-exclusive $238

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 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.

2027-01-15 → 2027-01-26 · Axel-exclusive $247

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 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.

2027-01-15 → 2027-01-27 · Axel-exclusive $247

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 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.

2027-01-15 → 2027-01-29 · Axel-exclusive $247

• Southwest Airlines WN1697: DEN 2027-01-15 08:55:00 → MDW 2027-01-15 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-29 09:20:00 → DEN 2027-01-29 11:00:00; nonstop; 160 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 14, 2027 · Return options
• Jan 16, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Jan 15, 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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