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Des Plaines Vacations from $269

Book a Hotel + Flight or Car together to unlock savings

Your Des Plaines Vacation

Reserve a Des Plaines vacation package that includes everything you need and nothing you don't. Good for cafes, nature and bars and pubs, think about basing yourself in the neighborhood of Rogers Park. If your trip to Des Plaines includes a little sightseeing, don't miss major attractions such as Allstate Arena, Rosemont Theatre and Fashion Outlets of Chicago. Stop dreaming and start adventuring. Explore the many options on Expedia today and finally put your Des Plaines vacation plans into motion!

The Latest Des Plaines Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 22 - Jan 24

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.6/10 - Excellent (2,391 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $373
    $269
    per traveler
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Jan 28 - Jan 31

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop MDW - ATL • Nonstop
    $704
    $483
    per traveler
    found 14 hours ago
    Pendry Chicago
  • Jan 14 - Jan 17

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,669 reviews)
    "The staff were more ghan helpful even when checking in after midnight The room was very spacious and clean The breakfast selection catered for everyone with good quality food foe everyone Had a wonderful stay, could not find a fault Thank you for your hospitality during our stsy"
    Reviewed November 9, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $572
    $394
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Jan 22 - Jan 24

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."
    Reviewed November 3, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $403
    $287
    per traveler
    found 1 day ago
    Le Méridien Essex Chicago
  • Jan 14 - Jan 17

    Eurostars Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (3,994 reviews)
    "Good but the condition of the room wasn’t the best."
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $484
    $347
    per traveler
    found 1 day ago
    Eurostars Magnificent Mile

Where to stay in Des Plaines

Explore Des Plaines, a welcoming city in the United States ideal for family and business travelers alike. Enjoy picnic areas and neighborhood parks, perfect for relaxation and outdoor fun. Nearby cities offer a vibrant atmosphere, ensuring a memorable experience for everyone.

Chicago

Discover Chicago, a vibrant city perfect for travelers seeking a blend of culture, family fun, and outdoor experiences. With attractions like the bustling Michigan Avenue for shopping, the iconic Navy Pier for entertainment, and McCormick Place for events, there's never a dull moment. Des Plaines, situated within Chicago, offers easy access to these highlights, making it a smart choice for your stay. Experience the best of the Windy City while enjoying its diverse offerings.

Arlington Heights

Experience the charm of Arlington Heights, an excellent hub for family travelers eager to explore attractions such as the Schaumburg Convention Center and the Metropolis Performing Arts Center. With a vibrant shopping scene and local sports facilities, this destination offers a delightful blend of activities for any vacation. Conveniently located about 6 miles by car from Des Plaines, Arlington Heights is a smart hotel booking choice for those seeking both leisure and city-related experiences.

Rosemont

If you are a traveler seeking a vibrant experience, look no further than Rosemont, a city known for its dynamic blend of entertainment and convenience. Enjoy the bustling atmosphere with attractions like the Donald E. Stephens Convention Center and the Parkway Bank Park Entertainment District, perfect for shopping and lively events. Located about 3 miles by car from Des Plaines, Rosemont offers easy access to the area’s highlights, making it a smart choice for your stay.

Park Ridge

Immerse yourself in Park Ridge, where family travelers and weekend adventurers can easily access vibrant attractions like the Donald E. Stephens Convention Center and the Parkway Bank Park Entertainment District. Offering a blend of city excitement and outdoor experiences, this charming city is an excellent base for exploring nearby educational venues like Northwestern University. Located about 3 miles by car from Des Plaines, Park Ridge makes a smart choice for your stay with its diverse activities and welcoming atmosphere.

Oakton

Travelers visiting the area often choose Oakton, especially those with a family or business focus, seeking close proximity to vibrant attractions. This welcoming neighborhood is near the Donald E. Stephens Convention Center for events, Northwestern University for educational pursuits, and the Parkway Bank Park Entertainment District for leisure activities. Located around Des Plaines, Oakton offers easy access to outdoor adventures, making it a smart choice for your next hotel booking.

Discover the most popular places to visit in Des Plaines

What to do in Des Plaines

Des Plaines Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Des Plaines vacation package cost?

You'll find cheap prices from $269 on Expedia for your Des Plaines getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Des Plaines costs.

What are the cheapest months to go to Des Plaines?

If you'd like to score a cheap Des Plaines vacation package, consider visiting in November, December and January. You'll usually find better rates on flights and hotels during these months — perfect for budget-conscious travelers.

How many days is enough for Des Plaines?

The ideal length of your Des Plaines vacation depends on what you'd like to do and see. Usually, a few days to a week will give you enough time to tick off all the leading attractions and explore some hidden treasures along the way.

How to find the best Des Plaines package deals?

Finding a cheap Des Plaines package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Des Plaines package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.

Is it cheaper to book a Des Plaines vacation as a package?

You can enjoy significant savings on your next Des Plaines break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.

When to book a vacation package to Des Plaines?

If you have your Des Plaines vacation dates finalized, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.

How to plan a trip to Des Plaines?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred season and the available activities will also help you decide when to visit Des Plaines.
  2. Set your budget: Consider costs such as transportation, flights and meals when calculating how much to set aside for your trip to Des Plaines. Then, pick a hotel that works with your budget, whether that's a wallet-friendly option or a more luxurious getaway.
  3. Explore Des Plaines using our trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Des Plaines. You can also save your must-visit places, collaborate with family and friends and organize your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Des Plaines, you can figure out the perfect length of your break. Put together a rough plan and allocate enough time to cover everything you want to see.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Des Plaines vacation package that brings all your bookings together.
  6. Book any day trips or activities: Now to the fun part — locking in everything you want to see and do. Browse some of the best things to do in Des Plaines and reserve your tickets in advance to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Des Plaines vacation packages?

Your Des Plaines trip is meant to be a relaxing escape from your daily routine, not a source of money worries. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.