How to Book Cheap Flights And Hotels

Learning how to book cheap flights and hotels can save you hundreds on your next vacation. Save first, sip champagne later. Here’s exactly how savvy travelers on Dealscrafted book smarter step by step.

Cheat Sheet

Search & Alerts: 

• Google Flights (set price alerts) →
• Skyscanner “Everywhere” + “Whole Month” →

Best-time-to-book

• Sundays often best; August cheapest month
• For many routes: ~39 days (domestic), ~49+ days (international) before departure. → Plan around these windows.

MileagePlus (United):

• Excursionist Perk if you’ll use it. Keep stacking with MileagePlus Shopping + MileagePlus X. → 

Alaska (Atmos):

• The unicorn: free stopover on one-way international award (visit 2 cities for ~1 award). Book via “multi-city.” → 

• Hilton: 5th Night Free on standard-room award stays (Silver+). →

• IHG: 4th Night Free when redeeming points with eligible IHG credit cards; Ambassador = complimentary weekend night + guaranteed 4pm late checkout at InterContinental (rate rules apply). →

• Southwest: Companion Pass at 135,000 qualifying points; no change fees (fare diff may apply). Reprice drops easily (esp. non-Basic). →

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Step 1. Pick travel dates the data way

• Circle your month then test Tuesdays/Wednesdays for returns. Midweek returns are frequently cheaper than Sunday/Monday.

• Work inside the “smart window”:
• Domestic: around ~39 days before departure.
• International: ~49+ days (Europe often 48+).
• Sunday tends to be the cheapest day to book (not to fly), and August has trended cheapest.

Do it: Open Google Flights → route → toggle “Track prices” (“Any dates” if flexible). Add Skyscanner’s Whole Month or Everywhere to see the exact cheap days and alt destinations.

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Step 2. Run the search like a pro

• Start: Google Flights (clean calendar view + alerts).  → Cross-check on Skyscanner (great for “Everywhere” and “Whole Month”)

• Compare structures: Round-trip vs two one-ways, open-jaw (fly into A, out of B), and multi-city (to add a purposeful long layover/stopover)

• Lock flexible fares when possible. If a drop hits later, you can reprice on many airlines without fees (fare difference applies). Southwest is especially easy here

Step 3. Book flights with the right loyalty play

A) United MileagePlus 

• Heads-up:  Focus on simple round-trip/open-jaw awards and partner sweet spots.

Stacking miles

• MileagePlus Shopping browser → earn miles at 1,000+ stores. 
• MileagePlus X app → buy eGift cards at checkout and stack more miles

• Points top-up: If you carry eligible Chase cards, transfer Ultimate Rewards to United 1:1

Search saver awards on United → activate MileagePlus Shopping → pay via MileagePlus X eGift where possible → transfer only what you need from Chase to United once you see seats.

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B) Alaska (now Atmos Rewards) — the “2 cities for 1 award” trick

• Killer perk: Free stopover on eligible one-way international awards (often up to ~14 days depending on partner). Book via Multi-city on Alaska’s site. Think NYC→Doha (stop 3–5 days)→Maldives for the same one-way award.

• Reality check: Availability tools matter; many stopovers must be at partner hubs and can be finicky online try segment searches or call if the website breaks.

Search partner space segment-by-segment → switch to Multi-city → insert your stopover city (partner hub) → price as 1 award.

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Step 4. Hotels: free nights you might be leaving on the table

Hilton Honors

• 5th Night Free on standard room award stays (5+ consecutive nights) for Silver, Gold, Diamond huge on resort weeks. 
• Play: If you’re close to 4 nights, push to 5 on points for a lower average nightly cost.

IHG One Rewards

• 4th Night Free (points) with eligible IHG credit cards sweet spot for long weekends.
• InterContinental Ambassador (paid status): Complimentary Weekend Night (2nd night free on the special rate) + guaranteed 4pm late checkout & upgrade at InterContinental (brand/rate rules apply). Use it for luxe city escapes.

Price cash vs points → if a 4- or 5-night stay, check IHG 4th-night-free or Hilton 5th-night-free math → book flexible rate where possible → set Google Hotels price-drop alerts to catch dips (toggle “Track hotel prices”). 

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Step 5. Date tricks that move the needle

• Return Tue/Wed when you can (weekend returns surge).
• Book on Sundays when feasible; track for drops. 
• Use 39/49+ guideposts (domestic/international) as a starting point, then let alerts steer you. 
• Open-jaw vs round-trip: flying into one city, out of another often saves versus backtracking and it unlocks more hotel options.
• Purposeful layovers: Use multi-city to create a full-day stop where you want it (or redeem Alaska/Atmos stopover for a real mini-trip)

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Step 6. Southwest: the flexible-flyer favorite

• Companion Pass: Earn 135,000 qualifying points (or 100 qualifying segments) in a calendar year; your companion flies for just taxes/fees.  Southwest Airlines
• Change/reprice with no fees (fare difference applies). If price drops, rebook and get points/credit back especially simple on non-Basic fares.

Book early on a refundable-ish fare type → set a weekly calendar reminder to reprice → when it’s cheaper, modify (or cancel/rebook on Basic) → pocket the credit/points.

Step 7. Put it all together

Goal: 6-night Europe getaway in shoulder season, 2 cities + beach.

1. Flights: Set Google Flights alerts for your city→Rome; also price open-jaw Rome→home from Barcelona; check Tue/Wed returns. 
2. Alternate play (miles): If you’ve got Alaska (Atmos) points, try NYC→Doha (3-day stop)→Athens on one award. 
3. Hotels:
   • Rome: 5-night Hilton on points → triggers 5th Night Free. 
   • Barcelona add-on: 2 InterContinental nights? Use Ambassador complimentary weekend night (rate rules). 
4. Safety net: Track hotel prices with Google Hotels to rebook if it dips. 

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FAQs

What’s the “best” time to book?

• Use data windows (≈39 days domestic; ≈49+ days international), then rely on alerts to pounce. Sundays trend cheaper to book

Is Alaska’s stopover really free on one-way awards?

• Yes on eligible one-way international awards (often up to ~14 days, partner/hub rules apply). Use Multi-city to force it.

Does Hilton’s 5th Night Free require status?

• Yes Silver or higher on standard room reward stays of 5+ consecutive nights.

IHG’s “4th Night Free” who gets it?

• Holders of eligible IHG credit cards when redeeming points on a 4-night (or longer) award.

Can I reprice Southwest if the fare drops?

• Yes no change fees; you’ll get a credit or points back (Basic requires cancel/rebook). 

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