Lea este artículo en español: De Chicago a México en las fiestas con puntos o en efectivo.
Every December, families from Pilsen, Little Village, Cicero, Waukegan and Milwaukee’s south side fill the flights to Guadalajara, León, Morelia and Zacatecas. If you are sitting on Chase, Amex or Capital One points and wondering whether they can cover the trip, the honest answer depends almost entirely on which town you are flying to.
The honest frame
For most interior hometowns, the nonstop from Chicago is Volaris or VivaAerobus, and neither has a US transferable-points partner or an alliance. There is no award seat to find. If you are going to Morelia, León, Zacatecas, Durango, San Luis Potosí or Aguascalientes, the points play is one of three things: fly United, American or Aeroméxico on points to Mexico City or Monterrey (or Guadalajara once Aeroméxico resumes it) and finish by bus or a domestic hop; pick a beach city where the legacy carriers and Southwest fly; or spend portal points as cash on the ultra-low-cost fare.
The nonstop map from Chicago, winter 2026-27
Our anchor is the Chicago Department of Aviation’s O’Hare international nonstop list dated September 1, 2026. “Confirmed” means the route is on that list or on the airline’s own page; “unconfirmed” means it appears only on aggregators or fare pages, which is where winter-only routes starting after September 1 show up. Midway’s official list could not be retrieved, so Midway routes rest on Volaris’s and Southwest’s pages plus aggregator summaries of the city’s June 2026 announcement.
| Destination | Confirmed nonstops | Unconfirmed (aggregators/fare pages only) |
|---|---|---|
| Guadalajara (GDL) | Volaris ORD ~2x daily; Viva ORD daily | Volaris MDW 4x weekly; Aeroméxico ORD suspended Aug 17-Dec 16, 2026, resumption shown Dec 10 |
| León/Bajío (BJX) | Volaris ORD ~4x weekly | Volaris MDW 3x weekly (Tue/Thu/Sat) |
| Morelia (MLM) | Volaris ORD daily | Volaris MDW daily |
| Zacatecas (ZCL) | None on the Sept 1 list | Volaris MDW 4x weekly |
| Durango (DGO) | None on the Sept 1 list | Volaris MDW 3x weekly (Tue/Thu/Sat) |
| San Luis Potosí (SLP) | Volaris MDW 4x weekly (Tue/Thu/Sat/Sun), launched June 2, 2026 | – |
| Aguascalientes (AGU) | Volaris MDW 4x weekly (volaris.com) | – |
| Querétaro (QRO) | Volaris ORD ~2x weekly | American ORD holiday-only, Thu-Sun from about Dec 17 |
| Monterrey (MTY) | United ORD daily (regional jet); Viva ORD ~4x weekly | – |
| Mexico City (MEX) | Aeroméxico ORD ~2x daily; American ORD; United ORD; Volaris ORD; Viva ORD | Viva ORD-NLU (AIFA) appears to end Oct 30, 2026 |
| Puebla (PBC) | – | Volaris ORD 3x weekly, new |
| Cancún (CUN) | American ORD; United ORD; Southwest MDW daily (2x Sat/Sun) | Frontier ORD daily, reportedly resumed Oct 8, 2026 |
| Puerto Vallarta (PVR) | United ORD | American ORD winter seasonal |
| Los Cabos (SJD) | American ORD; United ORD | Southwest MDW resumes Mar 11, 2027 (spring only) |
Not on the map: Spirit ceased operations May 2, 2026; Delta, Alaska and Sun Country fly no Chicago-Mexico nonstop; Viva’s O’Hare flights to León and Morelia ended in January 2026. Huatulco, Mazatlán, Oaxaca, Puerto Escondido, Mérida and Acapulco are connecting only.
The points options that actually exist
A caution: the issuer transfer pages and the United, American, Aeroméxico and LifeMiles award pages all blocked our checks, so figures marked “per” a third party are from those sites, dated July to October 2026. The Aeroplan chart is the one official document we could open.
- Air Canada Aeroplan on United (best documented). Aeroplan’s chart (version 2026-08) puts Mexico in its North America zone: economy one-way on Air Canada and select partners, United included, is 10,000 points for 501-1,500 miles and 12,500 for 1,501-2,750. Our computed distances put ORD-CUN at about 1,448 miles (10,000, but borderline; Aeroplan’s own table may use the higher band) and ORD-MEX at about 1,689 (12,500). A partner booking fee applies; Air Canada does not state the amount, and Milesopedia cites CAD $39. Transfers from Amex, Chase, Capital One and Bilt at 1:1; not Citi.
- United MileagePlus (dynamic). US-Mexico economy saver “from 5,000-20,000” one-way per AwardWallet (April 2026) and 10xTravel (June 2026). United cardholders save at least 10% on awards per United’s February 19, 2026 press release; no close-in fees; taxes not verified. Transfers from Chase and Bilt. The program that reaches Monterrey nonstop.
- American AAdvantage (dynamic). AA-operated Main Cabin to Mexico from 10,000 one-way per AwardWallet (July 2026); a June 2026 sale at 9,000 has expired. Transfers from Citi only.
- Avios on American. The British Airways partner chart since December 15, 2025 prices economy at 20,000 Avios one-way for 1,152-2,000 miles, covering ORD-CUN and ORD-MEX; Iberia matches on AA flights. No fuel surcharges; taxes not verified. BA takes Chase, Amex, Capital One (20% bonus through October 31) and Bilt. Pricier than AA’s own miles, but reachable from Chase and Amex.
- Aeroméxico Rewards: why Chicago is the expensive zone. Aeroméxico’s classic chart splits the US in two. “North America 1” (most of the US) prices economy one-way at 18,000 points low season and 22,000 high. “North America 2,” which is Canada, New York and Chicago, prices at 30,000 low and 38,000-39,000 high (sources conflict), and high season runs December 11, 2026 to January 10, 2027. Dynamic awards since August 2025 have “sharply increased,” and partner awards are not bookable online. Transfers from Amex at 1:1.6 (1:1.92 with the 20% bonus through October 30, 2026) and Capital One at 1:1; Citi dropped Aeroméxico January 25, 2026. Issuance fee MXN 323 online. From O’Hare, Aeroméxico is a cash carrier, not a points carrier.
- Avianca LifeMiles. No public chart, no fuel surcharges, award fee about $25. We could not verify any US-Mexico figure on United, so we quote none. Transfers from Amex, Capital One, Citi and Bilt; not Chase.
- Southwest to Cancún. Points tied to the fare at roughly 1.1 cents each per One Mile at a Time. Bags $45 first and $55 second (tickets bought on or after April 9, 2026), one free for A-List and cardholders; our gifts-and-cash post has the full bag table. Transfers from Chase and Bilt.
A family of four, worked out
Two adults, two kids, Chicago to Mexico City and back, one checked bag each. We will not invent December fares; plug in your own.
Option A, cash on an ultra-low-cost carrier. Volaris fare x 4 = [sample cash fare — check at booking]. Then the bags. Volaris publishes only maximums and shows the real price at checkout: its US fee sheet lists a first checked bag at up to $180 online (up to $228 at the airport) and a carry-on at up to $102 online (up to $180 at the gate). On a Zero fare with one checked bag each, the ceiling is $180 x 4 travelers x 2 directions = up to $1,440 on top of the fare. A Basic fare already includes one bag to 33 lb, and Plus includes a carry-on and a 55-lb bag, so price the fare families against each other. On VivaAerobus from O’Hare an extra 25-kg bag is $50 to $246 online each way per Viva’s fee page.
Option B, points on a legacy carrier. Aeroplan on United ORD-MEX: 12,500 x 4 x 2 = 100,000 points round trip, plus taxes (not verified for this route) and the partner booking fee. United’s own miles: 40,000 to 160,000 for the same four round trips at the 5,000-20,000 range, before the cardholder discount. Bags still cost money on United and American awards (United shows its US-Mexico fees only in its calculator; American’s first bag is $45 online), so add them before comparing.
Option C, Southwest to Cancún from Midway. Points at about 1.1 cents, plus $45/$55 bags (tickets bought on or after April 9, 2026), or one free bag each with the Southwest card. The simplest math here, but only if the beach is the destination.
The rule: if the Volaris fare plus the real bag total at checkout is less than what 100,000 Aeroplan points are worth to you, pay cash. And remember the award lands you in Mexico City or Monterrey, not Zacatecas; the bus home is extra money and hours.
When portal points beat a transfer
If the nonstop is Volaris, points touch it only as cash. Volaris is bookable in Capital One Travel at 1 cent per mile per AwardWallet (October 12, 2026). We could not verify whether Volaris appears in the Chase or Amex portals, and VivaAerobus is not listed in any portal per the same source. One cent per point against a nonstop to Morelia is a perfectly good use for a family that would otherwise pay cash.
The Milwaukee note
Mitchell has no nonstop to any interior Mexican city this winter. MKE’s only Mexico nonstops are Sun Country to Cancún from about December 18-19, 2026 (three days a week at first, daily from January 23 per the ALG flight guide), Southwest to Cancún on spring-break weekends in 2027, and package-only charters to Puerto Vallarta and Los Cabos from late January. For Guadalajara or León, ride Amtrak Hiawatha or Coach USA, or drive, to O’Hare or Midway, or take a one-stop from MKE on American or United via Dallas, Houston or O’Hare. Driving all the way? See our driving guide; either way, our kids-and-passports post covers the documents.
Aeroplan, United and British Airways all take Chase points at 1:1, which makes Chase the most flexible currency on this page. If you are considering a Chase Sapphire card, you can apply through our Chase referral link.
Disclosure: This is our personal Chase referral link. If you’re approved through it, we may earn a referral bonus, at no extra cost to you. You can always apply directly on Chase’s website. See our Advertising & Referral Disclosure.
Our take
For the interior cities, pay cash for the Volaris or Viva nonstop, buy the fare family that already includes the bag you need, and spend Capital One miles through its portal if you have them. Use transferable points for Mexico City or Monterrey: Aeroplan on United first because its pricing is published, United’s own miles second for the cardholder discount. Skip Aeroméxico points from Chicago in December. For Cancún, Southwest from Midway with the card’s free bag is hard to beat. And before you pay for a single bag, read the Paisano customs allowance post so you know what the gifts cost on the other end.
Sources
- Chicago Department of Aviation, O’Hare international nonstops (PDF, Sept 1, 2026)
- Aeroplan flight reward chart (PDF, version 2026-08) and zone definition
- Southwest Companion Pass and 2027 changes; Southwest optional travel charges
- Volaris ancillaries and fees (PDF) and baggage policy; VivaAerobus fees and charges
- United checked bags; American checked baggage policy
- Sun Country schedule release (June 9, 2026); ALG Milwaukee flight guide 2027 (PDF); MKE press release, July 16, 2026 (PDF)
- Third-party award figures: AwardWallet (United, April 2026; American, July 2026; Volaris/Viva portals, October 12, 2026), 10xTravel (June 2026), Milesopedia (Aeroplan partner fee), One Mile at a Time (Southwest value), and the Aeroméxico Rewards and British Airways partner charts as reported by those sites; United cardholder discount per United press release, February 19, 2026.
Fares, award prices and schedules change constantly; confirm on the airline’s site before you book. Points Capital is not a financial advisor.
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