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Chicago’s Travel Agency

Go Lazy. We’ll Handle the Rest.

Hot all-inclusive deals from Chicago, updated daily. Flights, hotel, transfers, drinks in your hand — we book it all so you don’t have to.

Hot Deals

Today’s Best Packages

Updated daily. Grab before they’re gone.

See All Deals →

How It Works

Three Steps to Lazy

No apps. No endless tabs. Just a phone call.

01

Browse Deals

Scan today’s hot packages. Or don’t — call us cold, we’ve got options not listed online.

02

Request in 30s

Tap a deal, fill in dates + party size, hit send. That’s it. No account.

03

Oksana Calls Back

Within 2 hours on business days. You get the final price, she handles the rest.

Based in Chicago

A Chicago all-inclusive travel agency built for Midwest families

Ministry of Lazy is a Chicago-based travel agency that specializes in one simple thing: affordable, all-inclusive Caribbean vacations that leave from O’Hare (ORD) or Midway (MDW). We are registered in Illinois as O&V Services LLC (IL LLC #16061905) and we work with every major tour operator flying the Chicago → Caribbean route, including Apple Vacations, Funjet, Pleasant Holidays, Southwest Vacations, Delta Vacations, United Vacations and VAX VacationAccess. That means when you call us for a quote on a week in Cancun or Punta Cana, you get the lowest tour-operator price any agent in Chicago can book — often lower than the big online booking sites once you strip out the junk fees.

We are not a call center. We are not an app. When you call 224-550-3760 , you get Oksana Korol — a licensed Illinois travel agent who personally books every trip. She knows which resorts in Cancun have the best kids clubs for Chicago families with toddlers, which Punta Cana properties are worth the long transfer to Uvero Alto, and which Jamaica all-inclusives still have direct non-stop flights out of Midway on Southwest. That kind of current, on-the-ground knowledge is the whole reason to use a Chicago travel agent instead of DIY-ing yourself into ten open browser tabs at 11 PM.

We serve the entire Chicagoland area, including downtown Chicago, the North Shore (Evanston, Wilmette, Winnetka, Glencoe, Highland Park, Lake Forest), the Northwest suburbs (Arlington Heights, Palatine, Schaumburg, Hoffman Estates, Barrington), the West suburbs (Oak Park, Naperville, Wheaton, Downers Grove, Elmhurst), the Southwest (Orland Park, Tinley Park, Oak Lawn), and Northwest Indiana commuters. We also have a big client base in the Ukrainian-American community around Ukrainian Village, Palatine, Des Plaines, Mount Prospect, and throughout the greater Chicago metro — Oksana is from Ukraine and speaks Ukrainian, Russian and English fluently.

If you searched for “all-inclusive vacation packages from Chicago”, “Chicago travel agent Cancun”, “cheap Caribbean deals from O’Hare”, “family resort packages from Midway”, or “Ukrainian travel agent in Chicago”, you are in the right place. Call us for a free quote — no email forms, no marketing funnels, no spam.

Hotel Database

Compare Hotels Like Never Before

Transfer time. Pool depth. Kids club age range. Food rating from people we actually trust. All the data in one place, zero marketing fluff.

Explore Hotels →

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Why Chicago Chooses All-Inclusive

Chicago to the Caribbean — the math that works

From December to April, Chicago gets long, brutal winters. A week on a warm beach is not a luxury for most Midwest families — it’s a sanity reset. Here is why all-inclusive packages from Chicago beat building your own trip piece by piece on the big booking sites.

Direct flights

Non-stop from ORD and MDW

Chicago is one of the best-connected US cities for Caribbean travel. Year-round non-stops from O’Hare to Cancun and Montego Bay on United and American; seasonal non-stops on Southwest out of Midway; plus easy one-stop connections to Punta Cana and Aruba via Miami, Charlotte, Houston and Atlanta. We only quote itineraries that actually work for your travel dates.

Bundled pricing

One price, one package

Flights, hotel, airport transfers, resort fees, taxes and tips are all bundled into the same per-person price you see on our quote. No surprise $180-per-night resort fee at check-in, no separate shuttle payment, no currency conversion mystery. This is what an all-inclusive travel agent in Chicago can negotiate that the big sites can’t.

Protection

Weather and delay coverage

Chicago winters come with snowstorm risk. Caribbean summer comes with hurricane risk. We always book with tour operators who offer rebooking or refunds when weather shuts the trip down — something DIY flight + hotel combinations cannot match. We also add affordable travel insurance on request.

Real human

A licensed Illinois agent

When your flight is delayed at O’Hare at 5 AM and you need someone to re-book the resort transfer in Cancun — you text Oksana Korol, not a chatbot in another country. That’s the difference between a Chicago travel agent and a booking-site 1-800 number.

Family rooms

Kids clubs and family suites

We know which Cancun and Punta Cana resorts have English-speaking kids clubs, which have waterparks for Chicago teens, which have baby pools, which offer nannies, and which let kids under 12 stay free. That’s years of field knowledge, not a search filter.

Free to use

Our quote costs you nothing

Travel agents in the US are paid commission by the tour operator after your trip is booked. You pay the same price as the tour-operator website — often less once we add our closed promos. A free Chicago travel agent consultation is basically the easiest win in travel planning.

Top Searches

The Caribbean destinations we book from Chicago

Chicago to Cancun — the most popular Caribbean run from the Midwest. Year-round non-stop flights from both ORD and MDW, flight time around 3 hours 45 minutes, no visa required for most US travelers, and the biggest selection of all-inclusive resorts anywhere in the Caribbean. We book everything from budget 3.5★ family hotels in the Hotel Zone to 5★ adults-only properties in Playa Mujeres and Riviera Maya (Playa del Carmen, Tulum). See Cancun →

Chicago to Punta Cana — slightly longer flight (about 4 hours 30 minutes) and often the best value on 4–5★ all-inclusive packages. The white-sand beaches in Bávaro and Uvero Alto are wider than Cancun and the water is calmer. Direct service from ORD is seasonal; we usually route through Miami or Charlotte the rest of the year. See Punta Cana →

Chicago to Jamaica — non-stop Chicago to Montego Bay (MBJ) on both United (ORD) and Southwest (MDW) during peak season. We book all three Jamaica resort zones: Montego Bay itself (closest to the airport), Ocho Rios (90-minute drive, waterfalls and excursions), and Negril (90 minutes, best beach on the island). Jamaica has more personality than any other Caribbean resort destination. See Jamaica →

Chicago to Aruba — the dry, sunny outlier. Aruba sits south of the Caribbean hurricane belt, so the weather is reliably perfect even during what would be hurricane season elsewhere. Flight time is about 5 hours 15 minutes; ORD direct is seasonal, otherwise we connect through Miami or Houston. The bonus: Aruba has US Customs pre-clearance, so when you land back in Chicago you arrive as a domestic passenger. See Aruba →

Not sure which to pick? Call 224-550-3760 and tell us your dates, party size and rough budget. We’ll suggest two or three options from the current week’s deals, all leaving from Chicago, in about ten minutes.

Client Reviews

People Who Were Lazy

And loved it.

"Oksana booked our family of five to Dreams Playa Mujeres in under an hour. Kids club, waterslides, and the price was honestly better than what I found on three comparison sites. She even remembered that my mom needed a ground-floor room."
Natalia K. · Cancun · March 2025
"I hate planning vacations. That’s why I called MoLazy. Text message, phone call, done. The transfer was waiting. Drinks were cold. I did nothing. 10/10."
Michael R. · Punta Cana · February 2025
"Finally an agent who speaks our language and actually knows what she’s selling. We went to Aruba in January and everything — hotel, flights, airport pickup — was exactly as promised."
Iryna P. · Aruba · January 2025

Ukrainian Travelers

Traveling on a Ukrainian passport?

We have a dedicated guide on visas, documents, and what to expect when you fly to Mexico or the Dominican Republic from Chicago.

Read the Guide →

Ready to Go Lazy?

Call Oksana. She’ll handle it.

No forms, no endless emails. Pick up the phone, tell her where you want to go, and start packing.

Mon–Sat 9am–8pm CT

Quick Request

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