5 Loyalty Deals Worth Booking This May 2026

TL;DR

Four deals made this list. The single deal to act on first: transfer Chase Ultimate Rewards to Marriott Bonvoy at a 55% bonus before June 30, 2026. At that ratio, 10,000 Chase points become 15,500 Bonvoy points. For a Bonvoy night priced at 25,000 points, the effective cost drops to roughly 16,129 Chase UR. Cash rates for comparable mid-tier properties can run $220–$280/night. The math: $250 ÷ 16,129 × 100 = 1.55 cpp. That clears the 1.5 cpp Chase UR baseline. Barely, but it clears it. Note that Marriott uses dynamic pricing, so the points cost for a specific hotel can vary.

The other three deals follow below, each with the same treatment: cash baseline, cpp, booking steps, and an honest read on availability. Use the MileIntel miles calculator to model your specific property before transferring.

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The Product

This article covers four distinct loyalty plays across hotel and airline programs active in May 2026. No deal appears here because it has an affiliate arrangement. Each one survived a cpp filter: the redemption must return more value than the transferable currency's baseline cash-out rate, and the booking must be executable by a reader who isn't a professional award-searcher.

Two deals involve transfer bonuses (Chase and Citi). One involves a hotel earn promotion. One is a Flying Blue promo award that expires soon.

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Deal 1: Flying Blue May Promo Awards — Europe Economy from 18,750 Miles One-Way

Cost: 18,750 Flying Blue miles + ~$160 taxes (one-way economy, select North America to Europe routes)Cash equivalent: $480 average for comparable economy fares on Air France/KLM in May–June 2026 based on sampled ITA Matrix results for JFK-CDG and BOS-AMSValue: $480 ÷ 18,750 × 100 = 2.56 cpp (outsized for economy)Window: Book by May 31, 2026. Travel through October 31, 2026.

What You Actually Get

Flying Blue Promo Rewards are a rotating monthly discount. May's offer cuts 25% off select economy and business class routes. Economy to Europe from the US starts at 18,750 miles one-way (down from 25,000). Business class promos are also live on some routes but the economy deal is the stronger cpp play given cash prices.

How to Book

1. Log into your Air France/KLM Flying Blue account at airfrance.com.
2. Search award availability directly on the Flying Blue portal — promo space is separate from standard saver space and shows up labeled as "Promo Rewards."
3. If you need to top up miles, Chase Ultimate Rewards transfers to Flying Blue 1:1. Chase also has a 20% transfer bonus to Flying Blue through May 27, 2026, meaning 10,000 Chase UR become 12,000 Flying Blue miles. That drops the effective Chase UR cost to roughly 15,625 UR for an 18,750-mile award.
4. Effective cpp with the transfer bonus: $480 ÷ 15,625 × 100 = 3.07 cpp on Chase UR. That is well above the 2.0 cpp Chase UR benchmark.

Availability Honest-Take

Promo award space is genuinely wider than standard saver space, but it is not unlimited. JFK-CDG and BOS-AMS show reasonable availability mid-May through June on Tuesday/Wednesday departures. Peak summer (July 4 week) is sparse. Search now; the booking deadline is May 31.

Why This Deal Exists

Flying Blue runs Promo Rewards monthly to fill unsold inventory on specific routes, and the discount is real, not a shell game with inflated base rates.

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Deal 2: Chase UR to Marriott Bonvoy at 55% Bonus

Cost: 16,129 Chase UR (effective, after bonus) for a Bonvoy night priced at 25,000 pointsCash equivalent: $250 average for a mid-tier Marriott property (sampled across Courtyard and Fairfield properties in secondary markets)Value: $250 ÷ 16,129 × 100 = 1.55 cpp on Chase UR (solid, not outsized)Window: Transfer by June 30, 2026. No travel deadline tied to the bonus itself; Bonvoy points do not expire with activity.

What You Actually Get

The 55% bonus means every 10,000 Chase UR transferred to Marriott Bonvoy becomes 15,500 Bonvoy points instead of the standard 10,000. Marriott uses dynamic pricing, but as an example, a night that costs 25,000 points would have an effective Chase UR cost of 16,129 UR (25,000 ÷ 1.55).

For context, Bonvoy's standard 1:1 transfer from Chase UR would cost 25,000 Chase UR for the same night, returning only $250 ÷ 25,000 × 100 = 1.0 cpp. The bonus adds 55 basis points of value.

See how Chase stacks up against Amex for hotel transfers in our Chase UR vs Amex MR comparison.

How to Book

1. Confirm the specific property and dates are available on points at Marriott.com before transferring anything.
2. In your Chase Ultimate Rewards portal, navigate to "Transfer to Travel Partners" and select Marriott Bonvoy. The 55% bonus applies automatically through June 30.
3. Transfer in the exact amount needed. Transfers are typically instant but can take up to a day.
4. Book the award directly through Marriott.com or the app using your Bonvoy balance.

Availability Honest-Take

Marriott award availability is generally wide. The constraint is finding a property where the dynamic points price provides good value against the cash rate. Mid-tier properties in major cities are often suburban Courtyards. In a secondary market or international destination, you can often find better hotels for the same number of points.

Why This Deal Exists

Chase runs periodic transfer bonuses to Marriott to drive UR engagement; this is one of the larger bonuses they have offered to Bonvoy in recent memory.

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Deal 3: Citi ThankYou to Preferred Hotels at 30% Bonus

Cost: 19,231 Citi ThankYou points (effective) for a 50,000-point Preferred Hotels nightCash equivalent: $350 average for a participating Preferred Hotels property at the I Prefer reward tier (sampled from PH&R's award catalog for boutique properties in Europe)Value: $350 ÷ 19,231 × 100 = 1.82 cpp on Citi TY (excellent)Window: Transfer by June 13, 2026.

Why This Deal Made the List

With a corrected value of 1.82 cpp, this deal is well above Citi TY's ~1.6 cpp baseline. This deal is on the list for two reasons: it provides excellent value and it unlocks boutique and independent hotels in cities where Marriott and Hyatt have no presence. If you need a specific property in, say, a small Italian hill town, and it is in the I Prefer catalog, this bonus makes the transfer a fantastic option.

The Citi ThankYou program guide has a full breakdown of which transfer partners return value.

How to Book

1. Search award availability at iprefer.com before transferring. Not all Preferred Hotels properties participate in the points redemption program.
2. Transfer Citi ThankYou points to I Prefer. The standard ratio is 1:2, and the 30% bonus applies automatically through June 13, making the effective ratio 1:2.6.
3. Book through iprefer.com using your I Prefer points balance.

Availability Honest-Take

Preferred Hotels award availability varies wildly by property. Some book out months in advance. Others have wide open space. Check availability first; do not transfer speculatively.

Why This Deal Exists

Citi and Preferred Hotels have a partnership that benefits both: Citi drives TY point redemptions, and PH&R gets exposure to credit card reward users.

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Deal 4: Wyndham 15,000 Bonus Points for 5-Night Stays

Cost: Standard points or cash for the stay (varies by property) + registration requiredBonus earned: 15,000 Wyndham points for any 5+ consecutive night stay at Hawthorn or WaterWalk extended-stay brands.Window: Register and book by June 30, 2026. Complete your stay by September 30, 2026.Cash equivalent of bonus: Wyndham points redeem at roughly 0.9–1.1 cpp. 15,000 points = $135–$165 in award value, or one free night at a mid-tier property.

What You Actually Get

This is a targeted promotion for longer stays at Wyndham's extended-stay brands. You must register for the offer, then book a stay of five or more consecutive nights directly with Wyndham at a participating Hawthorn Extended Stay or WaterWalk Extended Stay hotel. After the stay, you will receive 15,000 bonus points. The offer can only be earned once per member.

How to Book

1. Navigate to the promotion page on Wyndham's website and register your Wyndham Rewards account.
2. Book a stay of 5+ nights directly on wyndhamhotels.com at a Hawthorn or WaterWalk property.
3. Complete the stay by the September 30, 2026 deadline.

Availability Honest-Take

This deal is only useful if you have an upcoming need for a 5+ night stay and one of these specific brands is in your destination. It is not a deal to go out of your way for, but it's a valuable bonus if your plans align.

Why This Deal Exists

Wyndham is incentivizing longer bookings at its extended-stay brands to secure more valuable, multi-night reservations.