Denver (DEN) to Chicago (MDW), Jan 4–16, 2027: from $228 round trip

Denver (DEN) to Chicago (MDW), Jan 4–16, 2027: from $228 round trip on Axel, checked Nov 13, 2026. Lowest published fare: $228 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 4–16, 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.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

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 4–16, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $934 for 12 nights · 4★ Freehand Chicago, $73 a night, $878 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $229 a night, $2,743 for 12 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2027-01-04 → 2027-01-16 · Axel-exclusive $228

• Southwest Airlines WN1853 / WN1202: DEN 2027-01-04 11:15:00 → MDW 2027-01-04 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
  • WN1853: DEN 2027-01-04 11:15:00 → TUL 2027-01-04 13:55:00; layover at TUL: 70 minutes.
  • WN1202: TUL 2027-01-04 15:05:00 → MDW 2027-01-04 16:55:00.
• 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.

2027-01-04 → 2027-01-16 · Axel-exclusive $228

• Southwest Airlines WN1369 / WN2694: DEN 2027-01-04 11:25:00 → MDW 2027-01-04 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
  • WN1369: DEN 2027-01-04 11:25:00 → MCI 2027-01-04 14:05:00; layover at MCI: 105 minutes.
  • WN2694: MCI 2027-01-04 15:50:00 → MDW 2027-01-04 17:10:00.
• 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.

2027-01-04 → 2027-01-16 · Axel-exclusive $228

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

2027-01-04 → 2027-01-16 · Axel-exclusive $228

• Southwest Airlines WN1111 / WN537: DEN 2027-01-04 10:45:00 → MDW 2027-01-04 16:55:00; 1 stop(s) via ICT; 310 minutes. Local airport times.
  • WN1111: DEN 2027-01-04 10:45:00 → ICT 2027-01-04 13:05:00; layover at ICT: 120 minutes.
  • WN537: ICT 2027-01-04 15:05:00 → MDW 2027-01-04 16:55:00.
• 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.

2027-01-04 → 2027-01-16 · Axel-exclusive $228

• Southwest Airlines WN878 / WN878: DEN 2027-01-04 14:25:00 → MDW 2027-01-04 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
  • WN878: DEN 2027-01-04 14:25:00 → CVG 2027-01-04 18:50:00; layover at CVG: 90 minutes.
  • WN878: CVG 2027-01-04 20:20:00 → MDW 2027-01-04 20:30:00.
• 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.

2027-01-04 → 2027-01-16 · Axel-exclusive $238

• Southwest Airlines WN1699: DEN 2027-01-04 17:35:00 → MDW 2027-01-04 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.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Jan 3, 2027 · Return options
• Jan 5, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Jan 4, 2027 · return Jan 16, 2027: 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 priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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