Des Plaines Holidays

Photo by W. Ross Wells

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Des Plaines

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great property. Outstanding all the way around.

Reviewed on 13 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
It was totally worth the money as it had the best amenities, great views overlooking the city, and the river, staff was phenomenal, and couldn’t ask for more!

Reviewed on 15 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Food prices parking prices

Reviewed on 13 Aug 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.2/10 Wonderful! (1,831 reviews)
The bed and pillows were so comfortable! The linens super soft. Breakfast menu had good choices and excellent service. We loved Gigi

Reviewed on 14 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Great to be right amongst all the action, especially for summer fireworks!

Reviewed on 15 Aug 2025

Top hotels in Des Plaines

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €190 per night from 14 Sept to 15 Sept
€190
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,978 reviews)
"Great location. Hotel seems a bit dated"

Reviewed on 13 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €196 per night from 2 Sept to 3 Sept
€196
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,849 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on 11 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €145 per night from 4 Sept to 5 Sept
€145
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (3,681 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,923 properties in Des Plaines
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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Des Plaines

River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Des Plaines

Frequently asked questions

How much does a Des Plaines holiday package cost?
You'll find cheap prices from €1,148 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 holiday to Des Plaines costs.
What are the cheapest months to go to Des Plaines?
You can usually find lower rates and better availability in February, September and December. Explore our cheap Des Plaines holiday packages and you could score some excellent off-season deals.
How many days is enough for Des Plaines?
The ideal duration for your Des Plaines holiday depends on what you'd like to see. Generally, a few days to a week will give you enough time to visit all the top attractions and explore some hidden spots 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 holiday as a package?
You can enjoy significant savings on your next Des Plaines break by booking a customised holiday package. Click on the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Des Plaines?
If you have your Des Plaines holiday 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 travel: Check your schedule and pack your bags. Your preferred time of year and the activities available will also help you decide when to escape to Des Plaines.
  2. Plan your budget wisely: As well as the price of your hotel, you should factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Des Plaines.
  3. Decide how many days away: Start by making a list of all the activities and sights you want to get to in Des Plaines. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your airfare and accommodation: Once you've settled on your trip dates and duration, book the right Des Plaines holiday package for you.

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