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Chicago → Madison

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ORD → MSN1 adulteconomy

24 flight options · 2 airlines

Round-trip flights

Fri, Oct 30 – Mon, Nov 2

American Airlines
5:15 pmORD
1h 6m
Nonstop
6:21 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Oct 30 – Mon, Nov 2

United Airlines
10:05 pmORD
1h 2m
Nonstop
11:07 pmMSN
United Airlines
3:52 pmMSN
1h 13m
Nonstop
5:05 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Oct 31 – Sat, Nov 7

American Airlines
5:59 pmORD
1h 20m
Nonstop
7:19 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Oct 31 – Sat, Nov 7

United Airlines
1:45 pmORD
1h 5m
Nonstop
2:50 pmMSN
United Airlines
5:43 pmMSN
1h 22m
Nonstop
7:05 pmORD

Round-trip total · 1 adult · Taxes included

Tue, Nov 24 – Sun, Nov 29

American Airlines
5:15 pmORD
1h 6m
Nonstop
6:21 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Tue, Nov 24 – Sun, Nov 29

United Airlines
10:05 pmORD
1h 2m
Nonstop
11:07 pmMSN
United Airlines
3:52 pmMSN
1h 13m
Nonstop
5:05 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Mon, Nov 30

American Airlines
7:00 pmORD
1h 7m
Nonstop
8:07 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Mon, Nov 30

United Airlines
10:05 pmORD
1h 2m
Nonstop
11:07 pmMSN
United Airlines
3:52 pmMSN
1h 13m
Nonstop
5:05 pmORD

Round-trip total · 1 adult · Taxes included

Show 14 more flights

Sat, Nov 28 – Sat, Dec 5

American Airlines
7:00 pmORD
1h 7m
Nonstop
8:07 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 28 – Sat, Dec 5

United Airlines
1:45 pmORD
1h 5m
Nonstop
2:50 pmMSN
United Airlines
5:43 pmMSN
1h 22m
Nonstop
7:05 pmORD

Round-trip total · 1 adult · Taxes included

Tue, Dec 22 – Sun, Dec 27

American Airlines
5:15 pmORD
1h 6m
Nonstop
6:21 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Tue, Dec 22 – Sun, Dec 27

United Airlines
1:45 pmORD
1h 5m
Nonstop
2:50 pmMSN
United Airlines
3:52 pmMSN
1h 13m
Nonstop
5:05 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Dec 25 – Mon, Dec 28

American Airlines
5:15 pmORD
1h 6m
Nonstop
6:21 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Dec 25 – Mon, Dec 28

United Airlines
10:05 pmORD
1h 2m
Nonstop
11:07 pmMSN
United Airlines
3:52 pmMSN
1h 13m
Nonstop
5:05 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Dec 26 – Sat, Jan 2

American Airlines
7:00 pmORD
1h 7m
Nonstop
8:07 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Dec 26 – Sat, Jan 2

United Airlines
1:45 pmORD
1h 5m
Nonstop
2:50 pmMSN
United Airlines
5:43 pmMSN
1h 22m
Nonstop
7:05 pmORD

Round-trip total · 1 adult · Taxes included

Wed, Dec 30 – Sat, Jan 2

American Airlines
7:00 pmORD
1h 7m
Nonstop
8:07 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Wed, Dec 30 – Sat, Jan 2

United Airlines
3:50 pmORD
1h 12m
Nonstop
5:02 pmMSN
United Airlines
5:43 pmMSN
1h 22m
Nonstop
7:05 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Jan 15 – Mon, Jan 18

American Airlines
7:00 pmORD
1h 7m
Nonstop
8:07 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Jan 15 – Mon, Jan 18

United Airlines
1:45 pmORD
1h 5m
Nonstop
2:50 pmMSN
United Airlines
3:52 pmMSN
1h 13m
Nonstop
5:05 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Jan 22 – Mon, Jan 25

American Airlines
5:15 pmORD
1h 6m
Nonstop
6:21 pmMSN
American Airlines
8:41 pmMSN
1h 14m
Nonstop
9:55 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Jan 22 – Mon, Jan 25

United Airlines
1:45 pmORD
1h 5m
Nonstop
2:50 pmMSN
United Airlines
3:52 pmMSN
1h 13m
Nonstop
5:05 pmORD

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Oct 30 · One way

American Airlines
7:00 pmORD
1h 7m
Nonstop
8:07 pmMSN

One-way total · 1 adult · Taxes included

Fri, Oct 30 · One way

United Airlines
1:45 pmORD
1h 5m
Nonstop
2:50 pmMSN

One-way total · 1 adult · Taxes included

Make this trip yours

ORD ⇄ MSN

Economy

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

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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, American Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-10-30 · one wayAmerican AirlinesAA4005$165.002026-10-29T01:53:08Z
2026-10-30 · one wayUnited AirlinesUA1248$175.002026-10-29T01:53:08Z
2026-10-30 → 2026-11-02American AirlinesAA3346 / AA4005$295.002026-10-29T01:53:08Z
2026-10-30 → 2026-11-02United AirlinesUA1251 / UA1108$315.002026-10-29T01:53:08Z
2026-10-31 → 2026-11-07American AirlinesAA6266 / AA4005$295.002026-10-29T01:53:08Z
2026-10-31 → 2026-11-07United AirlinesUA1248 / UA5563$315.002026-10-29T01:53:08Z
2026-11-24 → 2026-11-29American AirlinesAA3346 / AA4005$368.762026-10-29T01:53:08Z
2026-11-24 → 2026-11-29United AirlinesUA1251 / UA5413$393.762026-10-29T01:53:08Z
2026-11-27 → 2026-11-30American AirlinesAA4005 / AA4005$368.762026-10-29T01:53:08Z
2026-11-27 → 2026-11-30United AirlinesUA1251 / UA1108$393.762026-10-29T01:53:08Z
2026-11-28 → 2026-12-05American AirlinesAA4005 / AA4005$331.882026-10-29T01:53:08Z
2026-11-28 → 2026-12-05United AirlinesUA1248 / UA5563$354.382026-10-29T01:53:08Z
2026-12-22 → 2026-12-27American AirlinesAA3346 / AA4005$354.002026-10-29T01:53:08Z
2026-12-22 → 2026-12-27United AirlinesUA1248 / UA5413$378.002026-10-29T01:53:08Z
2026-12-25 → 2026-12-28American AirlinesAA3346 / AA4005$346.632026-10-29T01:53:08Z
2026-12-25 → 2026-12-28United AirlinesUA1251 / UA1108$370.132026-10-29T01:53:08Z
2026-12-26 → 2027-01-02American AirlinesAA4005 / AA4005$346.632026-10-29T01:53:08Z
2026-12-26 → 2027-01-02United AirlinesUA1248 / UA5563$370.132026-10-29T01:53:08Z
2026-12-30 → 2027-01-02American AirlinesAA4005 / AA4005$339.262026-10-29T01:53:08Z
2026-12-30 → 2027-01-02United AirlinesUA5904 / UA5563$362.262026-10-29T01:53:08Z
2027-01-15 → 2027-01-18American AirlinesAA4005 / AA4005$295.002026-10-29T01:53:08Z
2027-01-15 → 2027-01-18United AirlinesUA1248 / UA1108$315.002026-10-29T01:53:08Z
2027-01-22 → 2027-01-25American AirlinesAA3346 / AA4005$295.002026-10-29T01:53:08Z
2027-01-22 → 2027-01-25United AirlinesUA1248 / UA1108$315.002026-10-29T01:53:08Z

2026-10-30 · one way · $165.00

  • American Airlines AA4005: ORD 2026-10-30 19:00:00 → MSN 2026-10-30 20:07:00; nonstop; 67 minutes. Local airport times.

2026-10-30 · one way · $175.00

  • United Airlines UA1248: ORD 2026-10-30 13:45:00 → MSN 2026-10-30 14:50:00; nonstop; 65 minutes. Local airport times.

2026-10-30 → 2026-11-02 · $295.00

  • American Airlines AA3346: ORD 2026-10-30 17:15:00 → MSN 2026-10-30 18:21:00; nonstop; 66 minutes. Local airport times.
  • American Airlines AA4005: MSN 2026-11-02 20:41:00 → ORD 2026-11-02 21:55:00; nonstop; 74 minutes. Local airport times.

2026-10-30 → 2026-11-02 · $315.00

  • United Airlines UA1251: ORD 2026-10-30 22:05:00 → MSN 2026-10-30 23:07:00; nonstop; 62 minutes. Local airport times.
  • United Airlines UA1108: MSN 2026-11-02 15:52:00 → ORD 2026-11-02 17:05:00; nonstop; 73 minutes. Local airport times.

2026-10-31 → 2026-11-07 · $295.00

  • American Airlines AA6266: ORD 2026-10-31 17:59:00 → MSN 2026-10-31 19:19:00; nonstop; 80 minutes. Local airport times.
  • American Airlines AA4005: MSN 2026-11-07 20:41:00 → ORD 2026-11-07 21:55:00; nonstop; 74 minutes. Local airport times.

2026-10-31 → 2026-11-07 · $315.00

  • United Airlines UA1248: ORD 2026-10-31 13:45:00 → MSN 2026-10-31 14:50:00; nonstop; 65 minutes. Local airport times.
  • United Airlines UA5563: MSN 2026-11-07 17:43:00 → ORD 2026-11-07 19:05:00; nonstop; 82 minutes. Local airport times.

2026-11-24 → 2026-11-29 · $368.76

  • American Airlines AA3346: ORD 2026-11-24 17:15:00 → MSN 2026-11-24 18:21:00; nonstop; 66 minutes. Local airport times.
  • American Airlines AA4005: MSN 2026-11-29 20:41:00 → ORD 2026-11-29 21:55:00; nonstop; 74 minutes. Local airport times.

2026-11-24 → 2026-11-29 · $393.76

  • United Airlines UA1251: ORD 2026-11-24 22:05:00 → MSN 2026-11-24 23:07:00; nonstop; 62 minutes. Local airport times.
  • United Airlines UA5413: MSN 2026-11-29 15:52:00 → ORD 2026-11-29 17:05:00; nonstop; 73 minutes. Local airport times.

2026-11-27 → 2026-11-30 · $368.76

  • American Airlines AA4005: ORD 2026-11-27 19:00:00 → MSN 2026-11-27 20:07:00; nonstop; 67 minutes. Local airport times.
  • American Airlines AA4005: MSN 2026-11-30 20:41:00 → ORD 2026-11-30 21:55:00; nonstop; 74 minutes. Local airport times.

2026-11-27 → 2026-11-30 · $393.76

  • United Airlines UA1251: ORD 2026-11-27 22:05:00 → MSN 2026-11-27 23:07:00; nonstop; 62 minutes. Local airport times.
  • United Airlines UA1108: MSN 2026-11-30 15:52:00 → ORD 2026-11-30 17:05:00; nonstop; 73 minutes. Local airport times.

2026-11-28 → 2026-12-05 · $331.88

  • American Airlines AA4005: ORD 2026-11-28 19:00:00 → MSN 2026-11-28 20:07:00; nonstop; 67 minutes. Local airport times.
  • American Airlines AA4005: MSN 2026-12-05 20:41:00 → ORD 2026-12-05 21:55:00; nonstop; 74 minutes. Local airport times.

2026-11-28 → 2026-12-05 · $354.38

  • United Airlines UA1248: ORD 2026-11-28 13:45:00 → MSN 2026-11-28 14:50:00; nonstop; 65 minutes. Local airport times.
  • United Airlines UA5563: MSN 2026-12-05 17:43:00 → ORD 2026-12-05 19:05:00; nonstop; 82 minutes. Local airport times.

2026-12-22 → 2026-12-27 · $354.00

  • American Airlines AA3346: ORD 2026-12-22 17:15:00 → MSN 2026-12-22 18:21:00; nonstop; 66 minutes. Local airport times.
  • American Airlines AA4005: MSN 2026-12-27 20:41:00 → ORD 2026-12-27 21:55:00; nonstop; 74 minutes. Local airport times.

2026-12-22 → 2026-12-27 · $378.00

  • United Airlines UA1248: ORD 2026-12-22 13:45:00 → MSN 2026-12-22 14:50:00; nonstop; 65 minutes. Local airport times.
  • United Airlines UA5413: MSN 2026-12-27 15:52:00 → ORD 2026-12-27 17:05:00; nonstop; 73 minutes. Local airport times.

2026-12-25 → 2026-12-28 · $346.63

  • American Airlines AA3346: ORD 2026-12-25 17:15:00 → MSN 2026-12-25 18:21:00; nonstop; 66 minutes. Local airport times.
  • American Airlines AA4005: MSN 2026-12-28 20:41:00 → ORD 2026-12-28 21:55:00; nonstop; 74 minutes. Local airport times.

2026-12-25 → 2026-12-28 · $370.13

  • United Airlines UA1251: ORD 2026-12-25 22:05:00 → MSN 2026-12-25 23:07:00; nonstop; 62 minutes. Local airport times.
  • United Airlines UA1108: MSN 2026-12-28 15:52:00 → ORD 2026-12-28 17:05:00; nonstop; 73 minutes. Local airport times.

2026-12-26 → 2027-01-02 · $346.63

  • American Airlines AA4005: ORD 2026-12-26 19:00:00 → MSN 2026-12-26 20:07:00; nonstop; 67 minutes. Local airport times.
  • American Airlines AA4005: MSN 2027-01-02 20:41:00 → ORD 2027-01-02 21:55:00; nonstop; 74 minutes. Local airport times.

2026-12-26 → 2027-01-02 · $370.13

  • United Airlines UA1248: ORD 2026-12-26 13:45:00 → MSN 2026-12-26 14:50:00; nonstop; 65 minutes. Local airport times.
  • United Airlines UA5563: MSN 2027-01-02 17:43:00 → ORD 2027-01-02 19:05:00; nonstop; 82 minutes. Local airport times.

2026-12-30 → 2027-01-02 · $339.26

  • American Airlines AA4005: ORD 2026-12-30 19:00:00 → MSN 2026-12-30 20:07:00; nonstop; 67 minutes. Local airport times.
  • American Airlines AA4005: MSN 2027-01-02 20:41:00 → ORD 2027-01-02 21:55:00; nonstop; 74 minutes. Local airport times.

2026-12-30 → 2027-01-02 · $362.26

  • United Airlines UA5904: ORD 2026-12-30 15:50:00 → MSN 2026-12-30 17:02:00; nonstop; 72 minutes. Local airport times.
  • United Airlines UA5563: MSN 2027-01-02 17:43:00 → ORD 2027-01-02 19:05:00; nonstop; 82 minutes. Local airport times.

2027-01-15 → 2027-01-18 · $295.00

  • American Airlines AA4005: ORD 2027-01-15 19:00:00 → MSN 2027-01-15 20:07:00; nonstop; 67 minutes. Local airport times.
  • American Airlines AA4005: MSN 2027-01-18 20:41:00 → ORD 2027-01-18 21:55:00; nonstop; 74 minutes. Local airport times.

2027-01-15 → 2027-01-18 · $315.00

  • United Airlines UA1248: ORD 2027-01-15 13:45:00 → MSN 2027-01-15 14:50:00; nonstop; 65 minutes. Local airport times.
  • United Airlines UA1108: MSN 2027-01-18 15:52:00 → ORD 2027-01-18 17:05:00; nonstop; 73 minutes. Local airport times.

2027-01-22 → 2027-01-25 · $295.00

  • American Airlines AA3346: ORD 2027-01-22 17:15:00 → MSN 2027-01-22 18:21:00; nonstop; 66 minutes. Local airport times.
  • American Airlines AA4005: MSN 2027-01-25 20:41:00 → ORD 2027-01-25 21:55:00; nonstop; 74 minutes. Local airport times.

2027-01-22 → 2027-01-25 · $315.00

  • United Airlines UA1248: ORD 2027-01-22 13:45:00 → MSN 2027-01-22 14:50:00; nonstop; 65 minutes. Local airport times.
  • United Airlines UA1108: MSN 2027-01-25 15:52:00 → ORD 2027-01-25 17:05:00; nonstop; 73 minutes. Local airport times.

More dates for this route