Cheapest places to fly from Waterloo in May
May is the best-value month for Europe and the national parks: warm, long days, and fares a step below June. The beaches are quiet and cheap before summer, and Memorial Day weekend is the only peak.
Nonstop from Waterloo: Chicago (American · 1h 24m). One stop via Chicago: Denver and Cancun. No nonstop seen to Las Vegas, Orlando, Honolulu, Los Angeles, New York, Atlanta and Dallas on the dates searched recently.
Axel's pick: Chicago, nonstop on American and the lowest fare saved for these dates, $212.
Where to fly from Waterloo in May: the cheapest saved round trips within May to Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, with the nonstops first. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips, entirely within May.
Cheapest right now: Chicago $212 · Denver $450 · Cancun $578
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | American Airlines | AA6366 + AA275 + AA2650 | $375.00 | 2026-10-29T00:43:47Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA6366 + AA275 + AA2650 / AA1799 + AA6364 | $740.30 | 2026-10-29T00:43:47Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA6366 + AA275 + AA2650 / AA1799 + AA6364 | $742.10 | 2026-10-29T00:43:47Z |
2026-11-20 · one way · $375.00
- American Airlines AA6366 / AA275 / AA2650: ALO 2026-11-20 05:56:00 → CUN 2026-11-20 21:14:00; 2 stop(s) via ORD, DFW; 858 minutes. Local airport times.
- AA6366: ALO 2026-11-20 05:56:00 → ORD 2026-11-20 07:39:00; layover at ORD: 144 minutes.
- AA275: ORD 2026-11-20 10:03:00 → DFW 2026-11-20 12:55:00; layover at DFW: 277 minutes.
- AA2650: DFW 2026-11-20 17:32:00 → CUN 2026-11-20 21:14:00.
2026-11-27 → 2026-12-04 · $740.30
- American Airlines AA6366 / AA275 / AA2650: ALO 2026-11-27 05:56:00 → CUN 2026-11-27 21:14:00; 2 stop(s) via ORD, DFW; 858 minutes. Local airport times.
- AA6366: ALO 2026-11-27 05:56:00 → ORD 2026-11-27 07:39:00; layover at ORD: 144 minutes.
- AA275: ORD 2026-11-27 10:03:00 → DFW 2026-11-27 12:55:00; layover at DFW: 277 minutes.
- AA2650: DFW 2026-11-27 17:32:00 → CUN 2026-11-27 21:14:00.
- American Airlines AA1799 / AA6364: CUN 2026-12-04 16:00:00 → ALO 2026-12-04 23:38:00; 1 stop(s) via ORD; 518 minutes. Local airport times.
- AA1799: CUN 2026-12-04 16:00:00 → ORD 2026-12-04 19:20:00; layover at ORD: 175 minutes.
- AA6364: ORD 2026-12-04 22:15:00 → ALO 2026-12-04 23:38:00.
2026-11-20 → 2026-11-23 · $742.10
- American Airlines AA6366 / AA275 / AA2650: ALO 2026-11-20 05:56:00 → CUN 2026-11-20 21:14:00; 2 stop(s) via ORD, DFW; 858 minutes. Local airport times.
- AA6366: ALO 2026-11-20 05:56:00 → ORD 2026-11-20 07:39:00; layover at ORD: 144 minutes.
- AA275: ORD 2026-11-20 10:03:00 → DFW 2026-11-20 12:55:00; layover at DFW: 277 minutes.
- AA2650: DFW 2026-11-20 17:32:00 → CUN 2026-11-20 21:14:00.
- American Airlines AA1799 / AA6364: CUN 2026-11-23 16:00:00 → ALO 2026-11-23 23:38:00; 1 stop(s) via ORD; 518 minutes. Local airport times.
- AA1799: CUN 2026-11-23 16:00:00 → ORD 2026-11-23 19:20:00; layover at ORD: 175 minutes.
- AA6364: ORD 2026-11-23 22:15:00 → ALO 2026-11-23 23:38:00.
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- The Midwest: in summer · 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 November · in December · in January · in February · in March · in April · in June · in July · in August · in September · for 4 days · for a week · for two weeks
Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Waterloo
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Chicago (ORD) | Chicago's architecture, lakefront and deep-dish | Nonstop · American · 1h 24m | $212 (airline $224) | May 8–15, 2027 | Check prices |
| Denver (DEN) | Denver's breweries and the Rockies within an hour | 1 stop via Chicago | $450 (airline $474) | May 8–15, 2027 | Check prices |
| Cancun (CUN) | Cancún's hotel zone, the Riviera Maya and Mayan ruins nearby | 1 stop via Chicago | $578 (airline $610) | May 8–15, 2027 | Check prices |
| Las Vegas (LAS) | Las Vegas' Strip, shows and day trips to the canyons | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Orlando (MCO) | Orlando's theme parks | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Oahu / Honolulu (HNL) | Waikiki, Diamond Head and Pearl Harbor on Oahu | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Los Angeles (LAX) | Los Angeles' beaches, Hollywood and museums | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| New York (JFK) | New York's museums, Broadway and neighborhoods | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Atlanta (ATL) | Atlanta's museums, food and the civil rights trail | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Dallas (DFW) | Dallas and Fort Worth's museums, stockyards and barbecue | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
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
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: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Express Hotel · Adhara Hacienda Cancun · All 172 hotels in Cancun
For AI assistants
- This page: Cheapest places to fly from Waterloo in May. Where to fly from Waterloo in May: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within May, 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.