Chicago isn’t just a vibrant city known for its skyline, deep-dish pizza, and jazz roots—it’s also a fantastic starting point for affordable getaways. As one of the busiest air travel hubs in the U.S., Chicago offers travelers a wide range of vacation package deals to destinations near and far. Whether you’re looking for a beach vacation, a city break, or an outdoor adventure, bundling your flight and hotel through vacation packages can help you save significantly on your next trip. These packages are not only budget-friendly but also time-saving, taking the stress out of travel planning. In this post, we’ll explore why Chicago is ideal for vacation deals, the top destinations you can visit without spending a fortune, and how to find the best travel packages available.
Why Choose Packages from Chicago
Booking a vacation package instead of individual components (like flights, hotels, and tours) is one of the smartest ways to travel on a budget. Here’s why:
- Lower Prices: Many travel sites offer exclusive discounts when you bundle flight and hotel together—sometimes saving up to 30% or more.
- Convenience: Booking everything at once saves time and ensures all parts of your trip align.
- Peace of Mind: With a package, you often get support if anything goes wrong (like cancellations or delays).
Chicago is especially great for finding deals thanks to its two major airports:
- O’Hare International Airport (ORD) – One of the largest and busiest airports in the world, with nonstop service to hundreds of domestic and international destinations.
- Midway International Airport (MDW) – Known for affordable carriers like Southwest and Frontier, it’s perfect for low-cost travel within the U.S.
With access to both full-service and budget airlines, Chicago gives travelers more flexibility and more competition—which usually means better prices.
Top Budget-Friendly Destinations from Chicago
Looking to get away without spending a fortune? Here are some affordable vacation destinations you can easily reach from Chicago.
1. Las Vegas, Nevada
- Average Package Price: $450–$750 (3–4 nights)
- Flight Time: Around 4 hours
- Top Attractions:
- The Strip’s casinos and shows
- Hoover Dam and Red Rock Canyon
- Fremont Street nightlife
- Best Travel Months: January–March and August (lower hotel prices)
2. Orlando, Florida
- Average Package Price: $400–$700 (3–5 nights)
- Flight Time: Around 2.5 hours
- Top Attractions:
- Walt Disney World and Universal Studios
- Kennedy Space Center
- International Drive shopping and dining
- Best Travel Months: Late January to early March; September
3. Cancun, Mexico
- Average Package Price: $600–$1,000 (4–5 nights, all-inclusive)
- Flight Time: Around 4 hours
- Top Attractions:
- All-inclusive beach resorts
- Mayan ruins at Tulum and Chichen Itza
- Snorkeling and nightlife in the Hotel Zone
- Best Travel Months: April–June and September–early December
4. Denver, Colorado
- Average Package Price: $400–$650 (3–4 nights)
- Flight Time: Around 2.5 hours
- Top Attractions:
- Rocky Mountain National Park
- Red Rocks Amphitheatre
- Local breweries and hiking trails
- Best Travel Months: May–June and September–October
5. New Orleans, Louisiana
- Average Package Price: $450–$700 (3–4 nights)
- Flight Time: Around 2 hours
- Top Attractions:
- French Quarter and Bourbon Street
- Historic cemeteries and jazz clubs
- Creole cuisine and riverboat tours
- Best Travel Months: April–May and October–November
6. San Juan, Puerto Rico
- Average Package Price: $550–$900 (4–5 nights)
- Flight Time: Around 5 hours
- Top Attractions:
- Old San Juan’s historic forts
- El Yunque Rainforest
- Condado and Isla Verde beaches
- Best Travel Months: May–June and mid-September to November
Finding the Cheapest Deals
Finding the best vacation package from Chicago doesn’t require luck—just a few smart strategies and the right tools. Top travel platforms like Expedia, Priceline, Kayak, and CheapCaribbean specialize in offering bundle deals that include flights, hotels, and sometimes even extras like car rentals or excursions. These platforms allow you to compare multiple options quickly, filter by budget or amenities, and often feature limited-time promotions.
Here are some actionable tips to help you score the lowest prices:
- Use Fare Alerts: Set up price alerts on Kayak or Google Flights for destinations you’re interested in. You’ll get notified when prices drop.
- Book in the Off-Season: Traveling during less busy times (like spring or fall) means you’ll avoid crowds and save money.
- Bundle Flights + Hotels: Booking both together on sites like Expedia or Priceline usually gives you a better rate than purchasing separately.
- Be Flexible with Your Dates: Even a one-day shift can save hundreds. Use flexible date search options to compare.
- Try Nearby Airports: In addition to O’Hare, search for deals flying out of Midway. You may find lower fares on budget carriers.
- Look for Flash Sales: Some platforms offer daily or weekly flash deals—Travelzoo and CheapCaribbean are known for these.
Types of Vacation Packages from Chicago
There’s a vacation package for just about every kind of traveler. Here are the most common types you’ll find when booking from Chicago:
All-Inclusive Resorts
Best for: Couples, honeymooners, and travelers who want a stress-free trip
Includes meals, drinks, entertainment, and sometimes tours—all in one price. Cancun, Punta Cana, and Montego Bay are popular choices.
Family Vacation Packages
Best for: Families with children
These often include kid-friendly accommodations, theme park tickets, and extras like breakfast or resort activities. Orlando is a go-to family spot.
Romantic Getaways
Best for: Couples and anniversaries
Think cozy mountain lodges, luxury beach resorts, or wine-country retreats. Packages may include spa treatments or romantic dinners.
City Breaks
Best for: Solo travelers, friend groups, or couples
Weekend getaways to places like New York, Nashville, or Toronto, often with centrally located hotels and optional city tours.
Adventure or Nature Packages
Best for: Active travelers and outdoor enthusiasts
Trips to Colorado, Utah, or even Costa Rica that include hiking, biking, rafting, or exploring national parks.
Each type of package offers a unique experience, and with so many airlines and routes departing from Chicago, there’s something for every budget and travel style.
Best Times to Book
Timing your booking wisely can make a big difference in how much you spend. Whether you’re planning months ahead or eyeing a last-minute escape, these tips will help you find the best deals.
- Book 1 to 3 Months in Advance: For most domestic or nearby international trips, this window gives you the best mix of availability and pricing.
- Travel During Shoulder Seasons: Spring (April–May) and fall (September–November) offer lower prices, fewer crowds, and mild weather.
- Avoid Major Holidays and Peak Times: Prices soar during summer break, Thanksgiving, and Christmas. If you must travel then, book 4–6 months in advance.
- Fly Midweek for Cheaper Rates: Tuesdays and Wednesdays are usually the most affordable days to fly, while weekends tend to cost more.
- Look for Early Week Sales: Airlines and travel platforms often release discounted fares on Mondays or Tuesdays.
By understanding these booking trends, you can stretch your budget and maybe even upgrade your trip.
Budget Travel Tips
Want to save even more on your next getaway from Chicago? These practical budget travel tips can help you stretch your vacation dollars:
- Pack Light and Use a Carry-On
Avoid checked bag fees by packing a carry-on, especially when flying budget airlines from Midway or O’Hare. - Compare Multiple Travel Sites
Prices vary by platform. Always compare offers from sites like Kayak, Expedia, Priceline, and CheapCaribbean before booking. - Travel During Off-Peak Seasons
Avoid high-demand dates like spring break or holidays. Traveling in the shoulder seasons (spring/fall) means better prices and fewer crowds. - Use Rewards and Travel Credit Cards
If you collect points or miles, check if they can be used for a portion of your vacation package—or help cover extras like upgrades or insurance. - Be Flexible with Your Dates
Adjusting your departure or return date by just a day or two can dramatically reduce your costs. - Sign Up for Deal Alerts
Use apps like Hopper or Google Flights to track price changes and get alerts when vacation packages drop in price. - Book Packages That Include Perks
Some vacation packages include free breakfasts, airport transfers, or activity credits—adding even more value for your money.
Recommended Travel Sites and Apps
Here are some of the best tools and platforms for finding cheap vacation packages from Chicago:
- Google Flights
Best for: Flexible date searching and fare alerts.
Allows you to explore destinations based on price and monitor flight trends. - Hopper
Best for: Price predictions and deal tracking.
Hopper tells you whether to book now or wait for a better deal using historical price data. - Skyscanner
Best for: Comparing multiple platforms at once.
Great for open-ended travelers who want to search “Everywhere” from Chicago. - Travelzoo
Best for: Curated travel deals and limited-time vacation packages.
Offers hand-picked trips with major savings, especially from big hubs like Chicago. - Expedia
Best for: Booking bundled packages with hotel, flight, and car rental.
Includes loyalty rewards and often has sitewide sales. - Priceline
Best for: Last-minute packages and “Express Deals.”
Offers big discounts for flexible travelers willing to book with limited details upfront. - CheapCaribbean
Best for: All-inclusive beach vacations.
Great for deals from Chicago to Cancun, Jamaica, and the Dominican Republic. - Kayak
Best for: Broad comparisons and filters.
Includes a useful “Explore” feature that shows where you can travel based on your budget.
Frequently Asked Questions
What are the cheapest months to travel from Chicago?
The best months for budget-friendly travel are January–March and September–November, when demand is lower and weather is still pleasant in many destinations.
How far in advance should I book a vacation package?
For most destinations, booking 1 to 3 months ahead offers the best combination of availability and price. For peak season trips, aim for 3–6 months in advance.
Are vacation packages really cheaper than booking separately?
Yes, vacation packages often include exclusive discounts when bundling flights and hotels, and sometimes even extras like breakfast or transfers.
Which airport in Chicago is better for cheap flights—O’Hare or Midway?
Midway Airport (MDW) typically has more low-cost carriers like Southwest and Frontier, but O’Hare (ORD) offers more international options and frequent sales. Check both when searching.
Can I find last-minute vacation deals from Chicago?
Absolutely. Platforms like Travelzoo, Priceline, and Expedia frequently feature last-minute packages, especially to popular destinations like Las Vegas or Orlando.
What are the best cheap beach destinations from Chicago?
Top affordable beach getaways include Cancun, San Juan (Puerto Rico), Myrtle Beach, and Fort Lauderdale—all with short flights and frequent deals.
Do vacation packages include travel insurance?
Not always. Travel insurance is usually offered as an add-on. Some credit cards provide limited insurance if you use them to book.
Can I customize a vacation package after booking?
That depends on the provider. Some allow you to upgrade rooms or add extras, while others are fixed to keep prices low. Always read the fine print.
What is the best day to depart for lower fares?
Tuesdays and Wednesdays are typically the cheapest days to fly. Weekend travel is almost always more expensive.
Is it safe to travel with budget vacation packages?
Yes, as long as you book through reputable platforms. Look for verified reviews and choose well-rated hotels and airlines to ensure a safe experience.