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Route overview: Madison to Chicago (ORD) flight deals

Madison (MSN) to Chicago (ORD), Jan 7, 2027: round trips from $320, one way from $185

Madison (MSN) to Chicago (ORD), Jan 7, 2027: round trips from $320, one way from $185 on Axel, checked Oct 29, 2026. Lowest published fares: $320 round trip, Axel-exclusive, American Airlines, nonstop, Jan 7–8, 2027; $185 one way, Axel-exclusive, American Airlines, nonstop, Jan 7, 2027; 1 adult, economy, checked Oct 29, 2026.

MSN → ORD1 adulteconomyOne way and round trips

30 flight options · 2 airlines

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. Thu, Jan 7 · One way

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Thu, Jan 7 · One way

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Thu, Jan 7 – Fri, Jan 8

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Thu, Jan 7 – Fri, Jan 8

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    5:59 amORD
    1h 10m
    Nonstop
    7:09 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Thu, Jan 7 – Sat, Jan 9

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    5:59 pmORD
    1h 20m
    Nonstop
    7:19 pmMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Thu, Jan 7 – Sat, Jan 9

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    5:59 amORD
    1h 10m
    Nonstop
    7:09 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Thu, Jan 7 – Sun, Jan 10

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Thu, Jan 7 – Sun, Jan 10

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    5:59 amORD
    1h 10m
    Nonstop
    7:09 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Thu, Jan 7 – Mon, Jan 11

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Thu, Jan 7 – Mon, Jan 11

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    8:45 amORD
    1h 16m
    Nonstop
    10:01 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Thu, Jan 7 – Wed, Jan 13

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Thu, Jan 7 – Wed, Jan 13

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    7:28 amORD
    1h 9m
    Nonstop
    8:37 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  13. Thu, Jan 7 – Thu, Jan 14

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Thu, Jan 7 – Thu, Jan 14

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    8:45 amORD
    1h 16m
    Nonstop
    10:01 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  15. Thu, Jan 7 – Fri, Jan 15

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Thu, Jan 7 – Fri, Jan 15

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    5:59 amORD
    1h 10m
    Nonstop
    7:09 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  17. Thu, Jan 7 – Sun, Jan 17

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Thu, Jan 7 – Sun, Jan 17

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    5:59 amORD
    1h 10m
    Nonstop
    7:09 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  19. Thu, Jan 7 – Mon, Jan 18

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Thu, Jan 7 – Mon, Jan 18

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    8:45 amORD
    1h 16m
    Nonstop
    10:01 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  21. Thu, Jan 7 – Tue, Jan 19

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    1:33 pmORD
    1h 9m
    Nonstop
    2:42 pmMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Thu, Jan 7 – Tue, Jan 19

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    3:42 pmORD
    1h 14m
    Nonstop
    4:56 pmMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  23. Thu, Jan 7 – Thu, Jan 21

    American Airlines
    5:00 amMSN
    1h 21m
    Nonstop
    6:21 amORD
    American Airlines
    7:14 amORD
    1h 13m
    Nonstop
    8:27 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Thu, Jan 7 – Thu, Jan 21

    United Airlines
    5:29 pmMSN
    1h 20m
    Nonstop
    6:49 pmORD
    United Airlines
    8:45 amORD
    1h 16m
    Nonstop
    10:01 amMSN

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

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1 of 24

Make this trip yours

MSN ⇄ ORD

Economy

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Explore this route

All dates for this routeJan 6, 2027 · Return optionsJan 8, 2027 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Madison (MSN) to Chicago (ORD), Jan 7, 2027: round trips from $320, one way from $185 on Axel, checked Oct 29, 2026. Lowest published fares: $320 round trip, Axel-exclusive, American Airlines, nonstop, Jan 7–8, 2027; $185 one way, Axel-exclusive, American Airlines, nonstop, Jan 7, 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)
2027-01-07 · one wayAmerican AirlinesAA448705:00:00→06:21:00 1h 21m nonstopAxel-exclusive $185.002026-10-29T01:30:37Z
2027-01-07 · one wayUnited AirlinesUA556317:29:00→18:49:00 1h 20m nonstopAxel-exclusive $195.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-08American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-08United AirlinesUA5563 / UA175817:29:00→18:49:00 1h 20m nonstop · 05:59:00→07:09:00 1h 10m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-09American AirlinesAA4487 / AA626605:00:00→06:21:00 1h 21m nonstop · 17:59:00→19:19:00 1h 20m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-09United AirlinesUA5563 / UA175817:29:00→18:49:00 1h 20m nonstop · 05:59:00→07:09:00 1h 10m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-10American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-10United AirlinesUA5563 / UA175817:29:00→18:49:00 1h 20m nonstop · 05:59:00→07:09:00 1h 10m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-11American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-11United AirlinesUA5563 / UA349717:29:00→18:49:00 1h 20m nonstop · 08:45:00→10:01:00 1h 16m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-12American AirlinesAA4487 / AA444105:00:00→06:21:00 1h 21m nonstop · 13:33:00→14:42:00 1h 09m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-12United AirlinesUA5563 / UA553017:29:00→18:49:00 1h 20m nonstop · 15:42:00→16:56:00 1h 14m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-13American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-13United AirlinesUA5563 / UA472517:29:00→18:49:00 1h 20m nonstop · 07:28:00→08:37:00 1h 09m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-14American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-14United AirlinesUA5563 / UA555917:29:00→18:49:00 1h 20m nonstop · 08:45:00→10:01:00 1h 16m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-15American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-15United AirlinesUA5563 / UA175817:29:00→18:49:00 1h 20m nonstop · 05:59:00→07:09:00 1h 10m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-16American AirlinesAA4487 / AA626605:00:00→06:21:00 1h 21m nonstop · 17:59:00→19:19:00 1h 20m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-16United AirlinesUA5563 / UA175817:29:00→18:49:00 1h 20m nonstop · 05:59:00→07:09:00 1h 10m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-17American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-17United AirlinesUA5563 / UA175817:29:00→18:49:00 1h 20m nonstop · 05:59:00→07:09:00 1h 10m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-18American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-18United AirlinesUA5563 / UA349717:29:00→18:49:00 1h 20m nonstop · 08:45:00→10:01:00 1h 16m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-19American AirlinesAA4487 / AA444105:00:00→06:21:00 1h 21m nonstop · 13:33:00→14:42:00 1h 09m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-19United AirlinesUA5563 / UA553017:29:00→18:49:00 1h 20m nonstop · 15:42:00→16:56:00 1h 14m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-20American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-20United AirlinesUA5563 / UA472517:29:00→18:49:00 1h 20m nonstop · 07:28:00→08:37:00 1h 09m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-21American AirlinesAA4487 / AA492305:00:00→06:21:00 1h 21m nonstop · 07:14:00→08:27:00 1h 13m nonstopAxel-exclusive $320.002026-10-29T01:30:37Z
2027-01-07 → 2027-01-21United AirlinesUA5563 / UA555917:29:00→18:49:00 1h 20m nonstop · 08:45:00→10:01:00 1h 16m nonstopAxel-exclusive $330.002026-10-29T01:30:37Z

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: Madison to Chicago (ORD) flight deals

2027-01-07 · one way · Axel-exclusive $185.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.

2027-01-07 · one way · Axel-exclusive $195.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.

2027-01-07 → 2027-01-08 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-08 07:14:00 → MSN 2027-01-08 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-08 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA1758: ORD 2027-01-08 05:59:00 → MSN 2027-01-08 07:09:00; nonstop; 70 minutes. Local airport times.

2027-01-07 → 2027-01-09 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA6266: ORD 2027-01-09 17:59:00 → MSN 2027-01-09 19:19:00; nonstop; 80 minutes. Local airport times.

2027-01-07 → 2027-01-09 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA1758: ORD 2027-01-09 05:59:00 → MSN 2027-01-09 07:09:00; nonstop; 70 minutes. Local airport times.

2027-01-07 → 2027-01-10 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-10 07:14:00 → MSN 2027-01-10 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-10 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA1758: ORD 2027-01-10 05:59:00 → MSN 2027-01-10 07:09:00; nonstop; 70 minutes. Local airport times.

2027-01-07 → 2027-01-11 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-11 07:14:00 → MSN 2027-01-11 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-11 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA3497: ORD 2027-01-11 08:45:00 → MSN 2027-01-11 10:01:00; nonstop; 76 minutes. Local airport times.

2027-01-07 → 2027-01-13 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-13 07:14:00 → MSN 2027-01-13 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-13 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA4725: ORD 2027-01-13 07:28:00 → MSN 2027-01-13 08:37:00; nonstop; 69 minutes. Local airport times.

2027-01-07 → 2027-01-14 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-14 07:14:00 → MSN 2027-01-14 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-14 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA5559: ORD 2027-01-14 08:45:00 → MSN 2027-01-14 10:01:00; nonstop; 76 minutes. Local airport times.

2027-01-07 → 2027-01-15 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-15 07:14:00 → MSN 2027-01-15 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-15 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA1758: ORD 2027-01-15 05:59:00 → MSN 2027-01-15 07:09:00; nonstop; 70 minutes. Local airport times.

2027-01-07 → 2027-01-17 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-17 07:14:00 → MSN 2027-01-17 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-17 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA1758: ORD 2027-01-17 05:59:00 → MSN 2027-01-17 07:09:00; nonstop; 70 minutes. Local airport times.

2027-01-07 → 2027-01-18 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-18 07:14:00 → MSN 2027-01-18 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-18 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA3497: ORD 2027-01-18 08:45:00 → MSN 2027-01-18 10:01:00; nonstop; 76 minutes. Local airport times.

2027-01-07 → 2027-01-19 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4441: ORD 2027-01-19 13:33:00 → MSN 2027-01-19 14:42:00; nonstop; 69 minutes. Local airport times.

2027-01-07 → 2027-01-19 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA5530: ORD 2027-01-19 15:42:00 → MSN 2027-01-19 16:56:00; nonstop; 74 minutes. Local airport times.

2027-01-07 → 2027-01-21 · Axel-exclusive $320.00

  • American Airlines AA4487: MSN 2027-01-07 05:00:00 → ORD 2027-01-07 06:21:00; nonstop; 81 minutes. Local airport times.
  • American Airlines AA4923: ORD 2027-01-21 07:14:00 → MSN 2027-01-21 08:27:00; nonstop; 73 minutes. Local airport times.

2027-01-07 → 2027-01-21 · Axel-exclusive $330.00

  • United Airlines UA5563: MSN 2027-01-07 17:29:00 → ORD 2027-01-07 18:49:00; nonstop; 80 minutes. Local airport times.
  • United Airlines UA5559: ORD 2027-01-21 08:45:00 → MSN 2027-01-21 10:01:00; nonstop; 76 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Madison (MSN) to Chicago (ORD) · Jan 7, 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 Madison to Chicago (ORD) 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.