Denver (DEN) to Chicago (MDW), Jan 10, 2027: round trips from $238, one way from $128

Denver (DEN) to Chicago (MDW), Jan 10, 2027: round trips from $238, one way from $128 on Axel, checked Oct 29, 2026. Lowest published fares: $238 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 10–11, 2027; $128 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 10, 2027; 1 adult, economy, checked Oct 29, 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, issued at the time 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 issuance times 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 lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Jan 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ Freehand Chicago, $70 total · 5★ Sofitel Chicago Magnificent Mile, $219 total
• Hotels in Chicago for these nights (Jan 10–12, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $158 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $125 total · 5★ Sofitel Chicago Magnificent Mile, $425 total
• Hotels in Chicago for these nights (Jan 10–13, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $196 total · 5★ Sofitel Chicago Magnificent Mile, $635 total
• Hotels in Chicago for these nights (Jan 10–14, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $304 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $215 total · 5★ Sofitel Chicago Magnificent Mile, $834 total
• Hotels in Chicago for these nights (Jan 10–15, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $377 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $234 total · 5★ Sofitel Chicago Magnificent Mile, $1,044 total
• Hotels in Chicago for these nights (Jan 10–16, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $447 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $260 total · 5★ Sofitel Chicago Magnificent Mile, $1,302 total
• Hotels in Chicago for these nights (Jan 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $520 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $286 total · 5★ Sofitel Chicago Magnificent Mile, $1,560 total
• Hotels in Chicago for these nights (Jan 10–18, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $601 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $305 total · 5★ Sofitel Chicago Magnificent Mile, $1,766 total
• Hotels in Chicago for these nights (Jan 10–19, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $674 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $376 total · 5★ Sofitel Chicago Magnificent Mile, $1,993 total
• Hotels in Chicago for these nights (Jan 10–20, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $758 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $447 total · 5★ Sofitel Chicago Magnificent Mile, $2,199 total
• Hotels in Chicago for these nights (Jan 10–21, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $843 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $518 total · 5★ Sofitel Chicago Magnificent Mile, $2,457 total
• Hotels in Chicago for these nights (Jan 10–22, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $916 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $537 total · 5★ Sofitel Chicago Magnificent Mile, $2,666 total
• Hotels in Chicago for these nights (Jan 10–23, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $989 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $634 total · 5★ Sofitel Chicago Magnificent Mile, $2,915 total
• Hotels in Chicago for these nights (Jan 10–24, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,062 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $731 total · 5★ Sofitel Chicago Magnificent Mile, $3,502 total

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2027-01-10 · one way · Axel-exclusive $128.25

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

2027-01-10 → 2027-01-11 · Axel-exclusive $237.50

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

2027-01-10 → 2027-01-12 · Axel-exclusive $247.00

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-12 09:20:00 → DEN 2027-01-12 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-10 → 2027-01-13 · Axel-exclusive $247.00

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-13 09:20:00 → DEN 2027-01-13 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-10 → 2027-01-14 · Axel-exclusive $247.00

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2027-01-14 10:50:00 → DEN 2027-01-14 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-10 → 2027-01-16 · Axel-exclusive $237.50

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 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.

2027-01-10 → 2027-01-17 · Axel-exclusive $247.00

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 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.

2027-01-10 → 2027-01-18 · Axel-exclusive $237.50

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 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.

2027-01-10 → 2027-01-20 · Axel-exclusive $247.00

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-20 09:20:00 → DEN 2027-01-20 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-10 → 2027-01-21 · Axel-exclusive $247.00

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 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.

2027-01-10 → 2027-01-22 · Axel-exclusive $247.00

• Southwest Airlines WN1699: DEN 2027-01-10 17:35:00 → MDW 2027-01-10 20:50:00; nonstop; 135 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.

2027-01-10 → 2027-01-24 · Axel-exclusive $247.00

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

Explore this route

• All dates for this route
• Jan 9, 2027 · Return options
• Jan 11, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Jan 10, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. 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 lowest saved totals among the shortlisted hotels in each star tier for those dates.
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