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. 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 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $264 total
• Hotels in Chicago for these nights (Jan 7–9, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $158 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $97 total · 5★ Sofitel Chicago Magnificent Mile, $522 total
• Hotels in Chicago for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $194 total · 5★ Sofitel Chicago Magnificent Mile, $724 total
• Hotels in Chicago for these nights (Jan 7–11, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $304 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $265 total · 5★ Sofitel Chicago Magnificent Mile, $943 total
• Hotels in Chicago for these nights (Jan 7–12, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $389 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $319 total · 5★ Sofitel Chicago Magnificent Mile, $1,149 total
• Hotels in Chicago for these nights (Jan 7–13, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $462 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $390 total · 5★ Sofitel Chicago Magnificent Mile, $1,359 total
• Hotels in Chicago for these nights (Jan 7–14, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $535 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $409 total · 5★ Sofitel Chicago Magnificent Mile, $1,558 total
• Hotels in Chicago for these nights (Jan 7–15, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $608 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $428 total · 5★ Sofitel Chicago Magnificent Mile, $1,768 total
• Hotels in Chicago for these nights (Jan 7–16, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $678 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $454 total · 5★ Sofitel Chicago Magnificent Mile, $2,026 total
• Hotels in Chicago for these nights (Jan 7–17, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $751 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $480 total · 5★ Sofitel Chicago Magnificent Mile, $2,284 total
• Hotels in Chicago for these nights (Jan 7–18, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $832 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $499 total · 5★ Sofitel Chicago Magnificent Mile, $2,490 total
• Hotels in Chicago for these nights (Jan 7–19, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $905 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $570 total · 5★ Sofitel Chicago Magnificent Mile, $2,717 total
• Hotels in Chicago for these nights (Jan 7–20, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $989 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $641 total · 5★ Sofitel Chicago Magnificent Mile, $2,923 total
• Hotels in Chicago for these nights (Jan 7–21, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,074 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $712 total · 5★ Sofitel Chicago Magnificent Mile, $3,181 total

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

• All dates for this route
• Jan 6, 2027 · Return options
• Jan 8, 2027 · Return options
• Hotels in Chicago with Axel

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.
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