New Haven (HVN) to Chicago (ORD), Dec 18, 2026: round trips from $246, one way from $109

New Haven (HVN) to Chicago (ORD), Dec 18, 2026: round trips from $246, one way from $109 on Axel, checked Nov 14, 2026. Lowest published fares: $246 round trip, Axel-exclusive, XP, nonstop, Dec 18–19, 2026; $109 one way, Axel-exclusive, XP, nonstop, Dec 18, 2026; 1 adult, economy, checked Nov 14, 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, labelled with the check date 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 check dates 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 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 (Dec 18–19, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $117 a night · 4★ Warwick Allerton - Chicago, $125 a night · 5★ Sofitel Chicago Magnificent Mile, $206 a night
• Hotels in Chicago for these nights (Dec 18–20, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $118 a night, $236 for 2 nights · 4★ Warwick Allerton - Chicago, $123 a night, $245 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $264 a night, $527 for 2 nights
• Hotels in Chicago for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $104 a night, $312 for 3 nights · 4★ Warwick Allerton - Chicago, $111 a night, $334 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $244 a night, $733 for 3 nights
• Hotels in Chicago for these nights (Dec 18–22, 2026 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $98 a night, $392 for 4 nights · 4★ Warwick Allerton - Chicago, $106 a night, $423 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $234 a night, $937 for 4 nights
• Hotels in Chicago for these nights (Dec 18–23, 2026 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey, $95 a night, $473 for 5 nights · 4★ Warwick Allerton - Chicago, $102 a night, $512 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $229 a night, $1,143 for 5 nights
• Hotels in Chicago for these nights (Dec 18–24, 2026 · 6 nights · 2 adults, 1 room): 3★ Hotel Versey, $95 a night, $572 for 6 nights · 4★ Warwick Allerton - Chicago, $101 a night, $608 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $225 a night, $1,350 for 6 nights
• Hotels in Chicago for these nights (Dec 18–25, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $98 a night, $689 for 7 nights · 4★ Warwick Allerton - Chicago, $101 a night, $704 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $221 a night, $1,549 for 7 nights
• Hotels in Chicago for these nights (Dec 18–26, 2026 · 8 nights · 2 adults, 1 room): 3★ Hotel Versey, $103 a night, $823 for 8 nights · 4★ Warwick Allerton - Chicago, $103 a night, $822 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $220 a night, $1,759 for 8 nights
• Hotels in Chicago for these nights (Dec 18–27, 2026 · 9 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $104 a night, $939 for 9 nights · 4★ Warwick Allerton - Chicago, $104 a night, $936 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $218 a night, $1,965 for 9 nights
• Hotels in Chicago for these nights (Dec 18–28, 2026 · 10 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $103 a night, $1,033 for 10 nights · 4★ Warwick Allerton - Chicago, $103 a night, $1,032 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $218 a night, $2,175 for 10 nights
• Hotels in Chicago for these nights (Dec 18–29, 2026 · 11 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $102 a night, $1,125 for 11 nights · 4★ Warwick Allerton - Chicago, $103 a night, $1,128 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $216 a night, $2,381 for 11 nights
• Hotels in Chicago for these nights (Dec 18–30, 2026 · 12 nights · 2 adults, 1 room): 3★ Hotel Versey, $101 a night, $1,214 for 12 nights · 4★ Warwick Allerton - Chicago, $102 a night, $1,222 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $216 a night, $2,588 for 12 nights
• Hotels in Chicago for these nights (Dec 18–31, 2026 · 13 nights · 2 adults, 1 room): 3★ Hotel Versey, $102 a night, $1,321 for 13 nights · 4★ Warwick Allerton - Chicago, $101 a night, $1,316 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $215 a night, $2,791 for 13 nights
• Hotels in Chicago for these nights (Dec 18 – Jan 1, 2027 · 14 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $109 a night, $1,529 for 14 nights · 4★ Warwick Allerton - Chicago, $109 a night, $1,519 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $232 a night, $3,241 for 14 nights

All hotels in Chicago

Route overview: New Haven to Chicago (ORD) flight deals

2026-12-18 · one way · Axel-exclusive $109

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.

2026-12-18 → 2026-12-19 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-19 19:07:00 → HVN 2026-12-19 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-20 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-20 19:07:00 → HVN 2026-12-20 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-21 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-21 19:07:00 → HVN 2026-12-21 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-22 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-22 19:07:00 → HVN 2026-12-22 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-24 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-24 19:07:00 → HVN 2026-12-24 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-25 19:07:00 → HVN 2026-12-25 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-26 19:07:00 → HVN 2026-12-26 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-28 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-28 19:07:00 → HVN 2026-12-28 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-29 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-29 19:07:00 → HVN 2026-12-29 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2026-12-30 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2026-12-30 19:07:00 → HVN 2026-12-30 22:30:00; nonstop; 143 minutes. Local airport times.

2026-12-18 → 2027-01-01 · Axel-exclusive $246

• XP XP421: HVN 2026-12-18 16:25:00 → ORD 2026-12-18 18:18:00; nonstop; 173 minutes. Local airport times.
• XP XP422: ORD 2027-01-01 19:07:00 → HVN 2027-01-01 22:30:00; nonstop; 143 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 17, 2026 · Return options
• Dec 19, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: New Haven (HVN) to Chicago (ORD) · Dec 18, 2026 · choose your return date: 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.
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