Cheapest places to fly from Chicago in November: flights from $140 one way, Nov 2026–Sep 2027

Flights for the months ahead

Lowest published fares for the months ahead: $238 round trip, Axel-exclusive, Frontier Airlines, nonstop, Sep 24–27, 2027; $140 one way, Axel-exclusive, Frontier Airlines, nonstop, Dec 1, 2026; 144 priced flights on 72 exact dates, 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.

Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.

Chicago (ORD) to Cancun (CUN): November 2026

Chicago (ORD) to Cancun (CUN): December 2026

Chicago (ORD) to Cancun (CUN): January 2027

Chicago (ORD) to Cancun (CUN): February 2027

Chicago (ORD) to Cancun (CUN): March 2027

Chicago (ORD) to Cancun (CUN): April 2027

Chicago (ORD) to Cancun (CUN): May 2027

Chicago (ORD) to Cancun (CUN): June 2027

Chicago (ORD) to Cancun (CUN): July 2027

Chicago (ORD) to Cancun (CUN): August 2027

Chicago (ORD) to Cancun (CUN): September 2027

Hotels in Cancun for these trips

Hotels: under a trip, hotels in Cancun 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 Cancun for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $122 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $147 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $412 total
• Hotels in Cancun for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $122 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $147 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $420 total
• Hotels in Cancun for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $288 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $343 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $941 total
• Hotels in Cancun for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $206 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $245 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $662 total
• Hotels in Cancun for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $122 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $147 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $396 total
• Hotels in Cancun for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $122 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $147 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $399 total
• Hotels in Cancun for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $292 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $364 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $945 total
• Hotels in Cancun for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $129 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $147 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $418 total
• Hotels in Cancun for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $130 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $147 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $416 total
• Hotels in Cancun for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $289 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $346 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $947 total
• Hotels in Cancun for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $125 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $153 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $421 total
• Hotels in Cancun for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $125 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $153 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $424 total
• Hotels in Cancun for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $290 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $389 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $953 total
• Hotels in Cancun for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $131 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $161 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $428 total
• Hotels in Cancun for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $144 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $168 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $434 total
• Hotels in Cancun for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $354 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $579 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,189 total
• Hotels in Cancun for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $249 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $557 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,003 total
• Hotels in Cancun for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $150 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $423 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $721 total
• Hotels in Cancun for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $154 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $432 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $729 total
• Hotels in Cancun for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $357 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $1,136 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,875.50 total
• Hotels in Cancun for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $152 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $522 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $865.50 total
• Hotels in Cancun for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $153 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $528 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $850.50 total
• Hotels in Cancun for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $147 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $497 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $763 total
• Hotels in Cancun for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $322 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $818 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,372 total
• Hotels in Cancun for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $138 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $222 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $543 total
• Hotels in Cancun for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $138 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $215 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $543 total
• Hotels in Cancun for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $314 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $452 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,253 total
• Hotels in Cancun for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $126 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $201 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $543 total
• Hotels in Cancun for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $126 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $205 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $536 total
• Hotels in Cancun for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $300 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $461 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,195 total
• Hotels in Cancun for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $127 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $188 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $510 total
• Hotels in Cancun for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $133 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $190 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $516 total
• Hotels in Cancun for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $303 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $451 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,206 total
• Hotels in Cancun for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $160 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $201 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $528 total
• Hotels in Cancun for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $173 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $201 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $528 total
• Hotels in Cancun for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $385 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $833 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,300 total
• Hotels in Cancun for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $143 total · 4★ Emporio Cancun Optional All Inclusive, $449 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $583 total
• Hotels in Cancun for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $131 total · 4★ Emporio Cancun Optional All Inclusive, $446 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $584 total
• Hotels in Cancun for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $372 total · 4★ Emporio Cancun Optional All Inclusive, $1,032 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,327 total
• Hotels in Cancun for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $155 total · 4★ Emporio Cancun Optional All Inclusive, $443 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $570 total
• Hotels in Cancun for these nights (Feb 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $173 total · 4★ Emporio Cancun Optional All Inclusive, $441 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $563 total
• Hotels in Cancun for these nights (Feb 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $408 total · 4★ Emporio Cancun Optional All Inclusive, $1,030 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,312 total
• Hotels in Cancun for these nights (Mar 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $173 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $426 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $563 total
• Hotels in Cancun for these nights (Mar 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $331 total · 4★ Emporio Cancun Optional All Inclusive, $1,034 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,312 total
• Hotels in Cancun for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $201 total · 4★ Pachamaya Holistic Wellness & Spa - Adults Only, $536 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $750 total
• Hotels in Cancun for these nights (Apr 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $162 total · 4★ Emporio Cancun Optional All Inclusive, $407 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $468 total
• Hotels in Cancun for these nights (Apr 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Antillano Cancun, $375 total · 4★ Emporio Cancun Optional All Inclusive, $938 total · 5★ The Reef 28 Hotel & Spa - Luxury Adults Only - All Suites, $1,092 total
• Hotels in Cancun for these nights (May 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (May 15–22, 2027 · 7 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Jun 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Jun 12–19, 2027 · 7 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Jul 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Jul 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Aug 6–9, 2027 · 3 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Aug 7–14, 2027 · 7 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Sep 4–11, 2027 · 7 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Sep 24–27, 2027 · 3 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive
• Hotels in Cancun for these nights (Sep 25 – Oct 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Ixchel Beach Hotel · 4★ Hotel Secreto · 5★ Atelier Playa Mujeres - Adults Only - All Inclusive

All hotels in Cancun

Route overview: Chicago to Cancun (CUN) flight deals

2026-11-19 → 2026-11-22 · Axel-exclusive $478.13

• American Airlines AA492: ORD 2026-11-19 10:02:00 → CUN 2026-11-19 15:00:00; nonstop; 238 minutes. Local airport times.
• American Airlines AA215: CUN 2026-11-22 14:20:00 → ORD 2026-11-22 17:40:00; nonstop; 260 minutes. Local airport times.

2026-11-19 → 2026-11-22 · Axel-exclusive $489.38

• United Airlines UA2371: ORD 2026-11-19 08:40:00 → CUN 2026-11-19 13:43:00; nonstop; 243 minutes. Local airport times.
• United Airlines UA1196: CUN 2026-11-22 13:16:00 → ORD 2026-11-22 16:18:00; nonstop; 242 minutes. Local airport times.

2026-11-24 · one way · Axel-exclusive $175.00

• Frontier Airlines F944: ORD 2026-11-24 07:59:00 → CUN 2026-11-24 12:55:00; nonstop; 236 minutes. Local airport times.

2026-11-24 · one way · Axel-exclusive $281.25

• American Airlines AA492: ORD 2026-11-24 10:02:00 → CUN 2026-11-24 15:00:00; nonstop; 238 minutes. Local airport times.

2026-11-28 → 2026-12-05 · Axel-exclusive $292.50

• Frontier Airlines F944: ORD 2026-11-28 07:12:00 → CUN 2026-11-28 12:30:00; nonstop; 258 minutes. Local airport times.
• Frontier Airlines F945: CUN 2026-12-05 11:38:00 → ORD 2026-12-05 14:38:00; nonstop; 240 minutes. Local airport times.

2026-11-28 → 2026-12-05 · Axel-exclusive $478.13

• American Airlines AA492: ORD 2026-11-28 10:02:00 → CUN 2026-11-28 15:00:00; nonstop; 238 minutes. Local airport times.
• American Airlines AA1910: CUN 2026-12-05 13:10:00 → ORD 2026-12-05 16:30:00; nonstop; 260 minutes. Local airport times.

2026-12-12 → 2026-12-19 · Axel-exclusive $318.50

• Frontier Airlines F944: ORD 2026-12-12 07:12:00 → CUN 2026-12-12 12:30:00; nonstop; 258 minutes. Local airport times.
• Frontier Airlines F945: CUN 2026-12-19 11:38:00 → ORD 2026-12-19 14:38:00; nonstop; 240 minutes. Local airport times.

2026-12-12 → 2026-12-19 · Axel-exclusive $520.63

• American Airlines AA492: ORD 2026-12-12 10:00:00 → CUN 2026-12-12 15:09:00; nonstop; 249 minutes. Local airport times.
• American Airlines AA1799: CUN 2026-12-19 16:09:00 → ORD 2026-12-19 19:29:00; nonstop; 260 minutes. Local airport times.

2026-12-25 → 2026-12-28 · Axel-exclusive $377.00

• Frontier Airlines F944: ORD 2026-12-25 07:59:00 → CUN 2026-12-25 12:55:00; nonstop; 236 minutes. Local airport times.
• Frontier Airlines F945: CUN 2026-12-28 11:38:00 → ORD 2026-12-28 14:38:00; nonstop; 240 minutes. Local airport times.

2026-12-25 → 2026-12-28 · Axel-exclusive $630.76

• United Airlines UA2371: ORD 2026-12-25 08:40:00 → CUN 2026-12-25 13:43:00; nonstop; 243 minutes. Local airport times.
• United Airlines UA1423: CUN 2026-12-28 15:11:00 → ORD 2026-12-28 18:13:00; nonstop; 242 minutes. Local airport times.

2027-01-07 → 2027-01-10 · Axel-exclusive $425.00

• American Airlines AA1907: ORD 2027-01-07 06:59:00 → CUN 2027-01-07 12:02:00; nonstop; 243 minutes. Local airport times.
• American Airlines AA215: CUN 2027-01-10 14:35:00 → ORD 2027-01-10 17:45:00; nonstop; 250 minutes. Local airport times.

2027-01-07 → 2027-01-10 · Axel-exclusive $435.00

• United Airlines UA2371: ORD 2027-01-07 08:40:00 → CUN 2027-01-07 13:43:00; nonstop; 243 minutes. Local airport times.
• United Airlines UA1672: CUN 2027-01-10 08:15:00 → ORD 2027-01-10 11:11:00; nonstop; 236 minutes. Local airport times.

2027-01-21 → 2027-01-24 · Axel-exclusive $425.00

• American Airlines AA1907: ORD 2027-01-21 06:59:00 → CUN 2027-01-21 12:02:00; nonstop; 243 minutes. Local airport times.
• American Airlines AA215: CUN 2027-01-24 14:35:00 → ORD 2027-01-24 17:45:00; nonstop; 250 minutes. Local airport times.

2027-01-21 → 2027-01-24 · Axel-exclusive $435.00

• United Airlines UA2371: ORD 2027-01-21 08:40:00 → CUN 2027-01-21 13:43:00; nonstop; 243 minutes. Local airport times.
• United Airlines UA1672: CUN 2027-01-24 08:15:00 → ORD 2027-01-24 11:11:00; nonstop; 236 minutes. Local airport times.

2027-02-04 → 2027-02-07 · Axel-exclusive $425.00

• American Airlines AA1907: ORD 2027-02-04 06:59:00 → CUN 2027-02-04 12:02:00; nonstop; 243 minutes. Local airport times.
• American Airlines AA215: CUN 2027-02-07 14:35:00 → ORD 2027-02-07 17:45:00; nonstop; 250 minutes. Local airport times.

2027-02-04 → 2027-02-07 · Axel-exclusive $435.00

• United Airlines UA2371: ORD 2027-02-04 08:40:00 → CUN 2027-02-04 13:43:00; nonstop; 243 minutes. Local airport times.
• United Airlines UA1672: CUN 2027-02-07 08:15:00 → ORD 2027-02-07 11:11:00; nonstop; 236 minutes. Local airport times.

2027-03-19 → 2027-03-22 · Axel-exclusive $340.60

• Frontier Airlines F944: ORD 2027-03-19 07:59:00 → CUN 2027-03-19 11:55:00; nonstop; 236 minutes. Local airport times.
• Frontier Airlines F945: CUN 2027-03-22 11:38:00 → ORD 2027-03-22 15:38:00; nonstop; 240 minutes. Local airport times.

2027-03-19 → 2027-03-22 · Axel-exclusive $569.86

• United Airlines UA2371: ORD 2027-03-19 08:40:00 → CUN 2027-03-19 12:43:00; nonstop; 243 minutes. Local airport times.
• United Airlines UA1423: CUN 2027-03-22 15:11:00 → ORD 2027-03-22 19:13:00; nonstop; 242 minutes. Local airport times.

2027-05-15 → 2027-05-22 · Axel-exclusive $266.00

• Frontier Airlines F944: ORD 2027-05-15 07:12:00 → CUN 2027-05-15 11:30:00; nonstop; 258 minutes. Local airport times.
• Frontier Airlines F945: CUN 2027-05-22 11:38:00 → ORD 2027-05-22 15:38:00; nonstop; 240 minutes. Local airport times.

2027-05-15 → 2027-05-22 · Axel-exclusive $365.76

• Delta Air Lines DL1717 / DL648: ORD 2027-05-15 06:20:00 → CUN 2027-05-15 14:30:00; 1 stop(s) via MSP; 490 minutes. Local airport times.
  • DL1717: ORD 2027-05-15 06:20:00 → MSP 2027-05-15 07:54:00; layover at MSP: 136 minutes.
  • DL648: MSP 2027-05-15 10:10:00 → CUN 2027-05-15 14:30:00.
• Delta Air Lines DL1963 / DL2879: CUN 2027-05-22 12:13:00 → ORD 2027-05-22 20:05:00; 1 stop(s) via ATL; 472 minutes. Local airport times.
  • DL1963: CUN 2027-05-22 12:13:00 → ATL 2027-05-22 15:55:00; layover at ATL: 170 minutes.
  • DL2879: ATL 2027-05-22 18:45:00 → ORD 2027-05-22 20:05:00.

2027-07-10 → 2027-07-17 · Axel-exclusive $294.00

• Frontier Airlines F944: ORD 2027-07-10 07:12:00 → CUN 2027-07-10 11:30:00; nonstop; 258 minutes. Local airport times.
• Frontier Airlines F945: CUN 2027-07-17 11:38:00 → ORD 2027-07-17 15:38:00; nonstop; 240 minutes. Local airport times.

2027-07-10 → 2027-07-17 · Axel-exclusive $425.26

• American Airlines AA1907: ORD 2027-07-10 06:59:00 → CUN 2027-07-10 11:02:00; nonstop; 243 minutes. Local airport times.
• American Airlines AA1799: CUN 2027-07-17 16:09:00 → ORD 2027-07-17 20:29:00; nonstop; 260 minutes. Local airport times.

2027-09-25 → 2027-10-02 · Axel-exclusive $245.00

• Frontier Airlines F944: ORD 2027-09-25 07:12:00 → CUN 2027-09-25 11:30:00; nonstop; 258 minutes. Local airport times.
• Frontier Airlines F945: CUN 2027-10-02 11:38:00 → ORD 2027-10-02 15:38:00; nonstop; 240 minutes. Local airport times.

2027-09-25 → 2027-10-02 · Axel-exclusive $363.13

• United Airlines UA1671: ORD 2027-09-25 15:46:00 → CUN 2027-09-25 19:44:00; nonstop; 238 minutes. Local airport times.
• United Airlines UA1672: CUN 2027-10-02 08:15:00 → ORD 2027-10-02 12:11:00; nonstop; 236 minutes. Local airport times.

More dates for this route

• Nov 19, 2026 · Return options
• Nov 27, 2026 · Return options
• Dec 8, 2026 · Return options
• Dec 19, 2026 · Return options
• Dec 29, 2026 · Return options
• Jan 8, 2027 · Return options
• Jan 19, 2027 · Return options
• Jan 30, 2027 · Return options
• Feb 19, 2027 · Return options
• May 14, 2027 · Return options
• Jul 9, 2027 · Return options
• Sep 25, 2027 · Return options
• Hotels in Cancun with Axel

Flights from Chicago

More trip ideas from Chicago

• 2027 total solar eclipse trips from Chicago
• A month somewhere warm from Chicago
• All-inclusive resort weeks from Chicago
• Bachelorette and bachelor party trips from Chicago, priced for 6
• Beach vacations from Chicago
• Big event trips from Chicago: Super Bowl, Coachella, Kentucky Derby and more
• Black heritage trips from Chicago
• Carnival trips from Chicago: Rio, Trinidad, Mardi Gras and more
• Cherry blossom trips from Chicago
• Christmas and New Year flights to the Middle East and Türkiye from Chicago
• Christmas flights to Africa from Chicago
• Christmas flights to Europe from Chicago
• Christmas flights to Mexico and Central America from Chicago
• Christmas flights to the Caribbean and South America from Chicago
• Christmas flights to the Philippines and Asia from Chicago
• Christmas market trips from Chicago
• College football bowl and playoff trips from Chicago
• Detty December: flights to Lagos and Accra from Chicago
• Día de Muertos trips from Chicago: Oaxaca, Mexico City, Pátzcuaro and more
• Diwali flights to India from Chicago
• Easter and Holy Week trips from Chicago: Seville, Rome, Antigua and more
• Fall foliage trips from Chicago
• Family vacations from Chicago, priced for 4
• Flights to your cruise port from Chicago
• Florida vacations from Chicago
• Food and wine trips from Chicago
• Formula 1 race trips from Chicago: Austin, Mexico City, Abu Dhabi and the 2027 calendar
• Fourth of July trips from Chicago
• Gay & LGBTQ+ friendly beach vacations from Chicago
• Gay & LGBTQ+ friendly cities to visit from Chicago
• Golf trips from Chicago
• Graduation trips from Chicago
• Grand Slam tennis trips from Chicago: Australian Open, Roland-Garros, Wimbledon and the US Open
• Group trips priced for 4 from Chicago
• Halloween trips from Chicago: Salem, New Orleans, Horror Nights, Derry and Transylvania
• Hawaii vacations from Chicago
• Holi in India: flights from Chicago
• Holiday flights to India and South Asia from Chicago
• Holiday lights and Christmas city trips from Chicago
• Honeymoon destinations from Chicago
• Irish heritage trips from Chicago
• Italian heritage trips from Chicago
• Japan trips from Chicago
• Labor Day weekend trips from Chicago
• Lapland and Santa trips from Chicago
• Lunar New Year flights from Chicago
• Marathon trips from Chicago: New York, Tokyo, Boston, London, Berlin and more
• Memorial Day weekend getaways from Chicago
• Midnight sun trips from Chicago
• MLK weekend getaways from Chicago
• Mountain and trekking trips from Chicago
• Music festival trips from Chicago
• National park trips from Chicago
• New Year's Eve trips from Chicago
• NFL international games from Chicago: London, Paris, Madrid, Munich and Mexico City
• Northern lights trips from Chicago
• October long weekend trips from Chicago
• Oktoberfest trips from Chicago
• Premier League and European football trips from Chicago
• Presidents' Day weekend getaways from Chicago
• Pride trips from Chicago: the biggest Pride events to fly to
• Ramadan and Eid trips from Chicago: Umrah and family visits
• Safari trips from Chicago
• Scuba diving and snorkeling trips from Chicago
• Ski trips from Chicago
• Solo trips from Chicago
• Songkran and New Year festivals in Asia from Chicago
• Spring break trips from Chicago
• Spring training trips from Chicago
• St. Patrick's Day trips from Chicago: Dublin, New York, Boston, Chicago and more
• Summer vacation trips from Chicago
• Surf trips from Chicago
• Thanksgiving trips from Chicago
• The best US cities to visit from Chicago
• Theme park trips from Chicago, priced for 4
• Three-week trips abroad from Chicago
• Tropical trips with no passport needed from Chicago
• Umrah trips from Chicago
• Valentine's Day getaways from Chicago
• Veterans Day weekend trips from Chicago
• Warm winter getaways from Chicago
• Whale watching trips from Chicago: Cabo, Maui, Sri Lanka, Dominica, Alaska, Iceland and more
• Winter break trips from Chicago
• Yoga and wellness retreats from Chicago
• Hawaii: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · in summer · for 4 days · for 5 days · for a week · for 10 days
• Mexico: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · for MLK weekend · in winter · in February · for 4 days · for 5 days · for a week
• The Caribbean: for Christmas · for spring break · for Presidents' Day weekend · in winter · in February · for 4 days · for 5 days · for a week
• Costa Rica: for Christmas · for spring break · in winter · for a week · for 10 days
• Central America: for Christmas · for spring break · in winter · for a week · for 10 days
• Europe: in summer · in May · in September · in December · for spring break · for Christmas · for a week · for 10 days · for two weeks
• Italy: in summer · in May · in June · in September · for Christmas · for a week · for 10 days · for two weeks
• Spain: in summer · in May · in September · for spring break · for a week · for 10 days
• Greece: in summer · in May · in June · in September · for a week · for 10 days · for two weeks
• Portugal: in summer · in May · in September · in winter · for 4 days · for a week · for 10 days
• Croatia: in summer · in June · in September · for a week · for 10 days
• Iceland: in summer · in winter · in September · for 4 days · for a week
• Scandinavia: in summer · in winter · in September · for 4 days · for a week · for 10 days
• Eastern Europe: in summer · in May · in September · in December · for a week · for 10 days
• England: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
• Scotland: in summer · in fall · for 4 days · for a week
• Ireland: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
• Japan: in April · in November · in winter · in summer · for a week · for 10 days · for two weeks
• South Korea: in spring · in fall · for a week · for 10 days
• Asia: in spring · in fall · in winter · for a week · for 10 days · for two weeks
• Southeast Asia: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks · for a month
• Thailand: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks
• Vietnam: in winter · in November · in February · in spring · for 10 days · for two weeks
• Bali: in summer · in winter · for 10 days · for two weeks · for a month
• India: in winter · in December · for two weeks · for a month
• Australia: in December · in January · in February · in September · for two weeks · for three weeks · for a month
• New Zealand: in December · in January · in February · for two weeks · for three weeks
• South America: in January · in February · in winter · for 10 days · for two weeks
• Colombia: in winter · in spring · for a week · for 10 days
• Peru: in summer · in May · in September · for 10 days · for two weeks
• The Middle East: in winter · for a week · for 10 days
• Turkey: in spring · in summer · in fall · for a week · for 10 days
• Africa: in winter · in fall · for 10 days · for two weeks
• South Africa: in winter · in fall · for 10 days · for two weeks
• Morocco: in spring · in fall · in winter · for a week · for 10 days
• Egypt: in winter · in fall · in spring · for a week · for 10 days
• Canada: in summer · in winter · in fall · for 3 days · for 4 days · for a week
• Florida: for spring break · for Christmas · for Thanksgiving · in winter · for 4 days · for 5 days · for a week
• California: for spring break · in summer · in winter · for 3 days · for 4 days · for a week
• The Pacific Northwest: in summer · in fall · for 3 days · for 4 days · for a week
• Alaska: in summer · in June · in July · in August · for 5 days · for a week · for 10 days
• The Southwest: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
• Arizona: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
• Utah: in winter · for Presidents' Day weekend · for MLK weekend · in spring · in summer · for 4 days · for a week
• The Rockies: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
• Colorado: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
• Montana and Wyoming: in summer · in winter · for a week · for 10 days
• Texas: in spring · in fall · for 3 days · for 4 days
• The Northeast: in fall · in summer · for Thanksgiving · for Christmas · for spring break · for 3 days · for 4 days · for a week
• New England: in fall · in summer · for 3 days · for 4 days · for a week
• The Southeast: in spring · in fall · for 3 days · for 4 days
• Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in December · in January · in February · in March · in April · in May · in June · in July · in August · in September · for 4 days · for a week · for two weeks

Cheapest places in November from other cities

Fares observed November 4 – 7, 2026. USD for the travelers shown.

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

Keep exploring

• Choose a destination

• Change travelers or cabin

Hotels in Cancun with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Cancun: the 8 best neighborhoods, ranked · Cancun hotels where a family of four can share one room

Hotel details in Cancun: Temptation at The Tower Cancún All Inclusive - Adults Only 4★ from $287 a night in the next 30 days · Paradisus Cancún – All Inclusive 5★ · Pachamaya Holistic Wellness & Spa - Adults Only 4★ from $49 a night in the next 30 days · Hyatt Ziva Cancun All Inclusive 4★ from $401 a night in the next 30 days · Hotel Riu Palace Riviera Maya 4★ · All 198 hotels in Cancun

For AI assistants

• This page: Cheapest places to fly from Chicago in November. Where to fly from Chicago in November: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within November, nonstop options first, and a link to search your own dates.
• Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.