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Route overview: Denver to Chicago (MDW) flight deals

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.

DEN → MDW1 adulteconomyOne way and round trips

15 flight options · 1 airline

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

January 2027

Flights for your trip

  1. Sun, Jan 10 · One way

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Sun, Jan 10 – Mon, Jan 11

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    10:05 amMDW
    5h 10m
    OMA · 1h 55m
    2:15 pmDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Sun, Jan 10 – Tue, Jan 12

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    9:20 amMDW
    2h 40m
    Nonstop
    11:00 amDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Sun, Jan 10 – Wed, Jan 13

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    9:20 amMDW
    2h 40m
    Nonstop
    11:00 amDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Sun, Jan 10 – Thu, Jan 14

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    10:50 amMDW
    2h 40m
    Nonstop
    12:30 pmDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Sun, Jan 10 – Sat, Jan 16

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    10:10 amMDW
    5h 10m
    MKE · 1h 45m
    2:20 pmDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Sun, Jan 10 – Sun, Jan 17

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    4:25 pmMDW
    2h 45m
    Nonstop
    6:10 pmDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Sun, Jan 10 – Mon, Jan 18

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    10:05 amMDW
    5h 10m
    OMA · 1h 55m
    2:15 pmDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Sun, Jan 10 – Wed, Jan 20

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    9:20 amMDW
    2h 40m
    Nonstop
    11:00 amDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Sun, Jan 10 – Thu, Jan 21

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    10:50 amMDW
    2h 40m
    Nonstop
    12:30 pmDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Sun, Jan 10 – Fri, Jan 22

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    9:20 amMDW
    2h 40m
    Nonstop
    11:00 amDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Sun, Jan 10 – Sun, Jan 24

    Southwest Airlines
    5:35 pmDEN
    2h 15m
    Nonstop
    8:50 pmMDW
    Southwest Airlines
    4:25 pmMDW
    2h 45m
    Nonstop
    6:10 pmDEN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

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1 of 12

Make this trip yours

DEN ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeJan 9, 2027 · Return optionsJan 11, 2027 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

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.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2027-01-10 · one waySouthwest AirlinesWN169917:35:00→20:50:00 2h 15m nonstopAxel-exclusive $128.252026-10-29T01:04:33Z
2027-01-10 → 2027-01-11Southwest AirlinesWN1699 / WN1523 + WN250917:35:00→20:50:00 2h 15m nonstop · 10:05:00→14:15:00 5h 10m 1 stop via OMAAxel-exclusive $237.502026-10-29T01:04:33Z
2027-01-10 → 2027-01-12Southwest AirlinesWN1699 / WN26417:35:00→20:50:00 2h 15m nonstop · 09:20:00→11:00:00 2h 40m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-13Southwest AirlinesWN1699 / WN26417:35:00→20:50:00 2h 15m nonstop · 09:20:00→11:00:00 2h 40m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-14Southwest AirlinesWN1699 / WN12017:35:00→20:50:00 2h 15m nonstop · 10:50:00→12:30:00 2h 40m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-15Southwest AirlinesWN1699 / WN26417:35:00→20:50:00 2h 15m nonstop · 09:20:00→11:00:00 2h 40m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-16Southwest AirlinesWN1699 / WN598 + WN3217:35:00→20:50:00 2h 15m nonstop · 10:10:00→14:20:00 5h 10m 1 stop via MKEAxel-exclusive $237.502026-10-29T01:04:33Z
2027-01-10 → 2027-01-17Southwest AirlinesWN1699 / WN460617:35:00→20:50:00 2h 15m nonstop · 16:25:00→18:10:00 2h 45m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-18Southwest AirlinesWN1699 / WN1523 + WN250917:35:00→20:50:00 2h 15m nonstop · 10:05:00→14:15:00 5h 10m 1 stop via OMAAxel-exclusive $237.502026-10-29T01:04:33Z
2027-01-10 → 2027-01-19Southwest AirlinesWN1699 / WN26417:35:00→20:50:00 2h 15m nonstop · 09:20:00→11:00:00 2h 40m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-20Southwest AirlinesWN1699 / WN26417:35:00→20:50:00 2h 15m nonstop · 09:20:00→11:00:00 2h 40m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-21Southwest AirlinesWN1699 / WN12017:35:00→20:50:00 2h 15m nonstop · 10:50:00→12:30:00 2h 40m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-22Southwest AirlinesWN1699 / WN26417:35:00→20:50:00 2h 15m nonstop · 09:20:00→11:00:00 2h 40m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z
2027-01-10 → 2027-01-23Southwest AirlinesWN1699 / WN598 + WN3217:35:00→20:50:00 2h 15m nonstop · 10:10:00→14:20:00 5h 10m 1 stop via MKEAxel-exclusive $237.502026-10-29T01:04:33Z
2027-01-10 → 2027-01-24Southwest AirlinesWN1699 / WN460617:35:00→20:50:00 2h 15m nonstop · 16:25:00→18:10:00 2h 45m nonstopAxel-exclusive $247.002026-10-29T01:04:33Z

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.

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

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.
  • Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Denver to Chicago (MDW) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.