Total Prizes:
$9,345,689
Active Sweepstakes:
88
Ad Placeholder 728×90
(Top Banner Ad)

Paddy’s Irish Whiskey Chicago St. Paddy’s Day Trip Giveaway

Posted Date: February 11, 2026
Enter for a chance to win a trip for two to Chicago for the 2027 St. Patrick’s Day celebration, plus daily instant win prizes along the way.

Mom-to-Mom Tip

What’s better than Chicago for St. Patty’s Day! This one’s a fun combo because you get one entry into the big trip drawing, and you can also take a quick daily shot at instant win prizes. The grand prize odds are always tougher, but the daily game makes it easy to stay in it without overthinking it.

New to Sweepstakes? Start Here

If you’re new to online sweepstakes, this page walks you through exactly how it works, from entry limits and instant wins to avoiding scams and improving odds. 

Read my How to Win guide →
Promotional graphic that says “Enter for your chance to win a trip to St. Paddy’s Day 2027” in bold black and green lettering on a light background with green shamrock accents. St. Paddy’s Day 2027 trip sweepstakes artwork promoting a Chicago St. Patrick’s Day travel prize. Enter-to-win St. Paddy’s Day 2027 trip giveaway image with festive shamrocks and large “Win a trip” headline.

NEW

Total Number of Prizes: 101

Grand Prize ARV: $2,700

Total ARV of All Prizes: $7,200

Entry Frequency: Daily Entry

Eligibility:

All states

Start Date: January 1, 2026

End Date: March 31, 2026

Prize Description:

One winner will score a trip for two to Chicago for the 2027 St. Patrick’s Day celebration, two hotel nights, and a $500 gift card.

There are also instant win prizes, including a Paddy’s cocktail kit and Venmo credits.

Includes travel.

Who’ll Love This (and Who Won’t)

You only get one entry total into the grand prize trip drawing, but you can play the instant win game once per day during the promotion. Instant win prizes are limited to one per person/household for the whole promotion, so if you win once, you’re done on instant wins.
Sweepstakes Mom logo featuring Elizabeth, a friendly sweepstakes expert and prize giveaway brand

How to Enter:

Online entry form + instant win game

Enter Here

All Prizes

Grand Prize: Trip for two (winner + 1 guest) to Chicago, IL for the 2027 St. Patrick’s Day celebration;

  • includes round-trip coach airfare for two (or a $500 gift card toward ground transportation if winner lives within 250 miles of Chicago)
  • 2 nights hotel (1 room, double occupancy)
  • one $500 gift card
    ARV: $2,700

Instant Win Prize: (50 winners)  Paddy’s Cocktail Kit.
ARV: $70

Instant Win Prize: (50 winners) $20 Venmo credit.
ARV: $20

Official Rules - Click Here

Why Should You Enter:

This is worth entering because it’s not just a single drawing, there’s a daily instant win play that gives you more chances to walk away with something. The effort is simple (register once, then quick daily plays if you want), and the grand prize is a clear, easy-to-understand trip package. If you like sweepstakes you can casually keep in rotation, this one fits nicely.

A Little Heads Up

You only get one entry total into the grand prize trip drawing, but you can play the instant win game once per day during the promotion. Instant win prizes are limited to one per person/household for the whole promotion, so if you win once, you’re done on instant wins.

Frequently Asked Questions:

Is this sweepstakes free to enter?

Sure is! This sweepstakes includes a free entry option, and buying something doesn’t change your chances one bit.

How and when will the winner be notified?

The potential winners are contacted by phone and/or email, and you’ll need to respond quickly to claim and confirm eligibility.

Not sure what a real winner notification looks like? See real examples of actual sweepstakes winner emails on our How to Know If You Won page.

Is this sweepstakes legitimate?

Yes—this is a legitimate promotion backed by official rules and run by Paddy’s sponsor Sazerac Company, Inc., with Million Dollar Media listed as the administrator.
Explore more Everyday Wins Sweepstakes or Daily Entry Sweepstakes.
Ad Placeholder 300×250 (Sidebar Ad)
Ad Placeholder 300×600 (Sidebar Ad #2)
Ad Placeholder 300×250
(Sidebar Bottom Ad)
Ad Placeholder (In-Post Banner)