Chicago Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Trump International Hotel & Tower Chicago
Park Hyatt Chicago
Virgin Hotels Chicago
The Royal Sonesta Chicago River North

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

Ready to book your vacation to Chicago?

 

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Chicago Hotel Deals

InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $335 per night from Jul 8 to Jul 9
CA $335
CA $437 total
Jul 8 - Jul 9
includes taxes & fees
9/10 Wonderful! (1,987 reviews)
"Excellent location"

Reviewed on Jul. 6, 2025

InterContinental Chicago Magnificent Mile by IHG
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 CA $162 per night from Aug 5 to Aug 6
CA $162
CA $190 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,866 reviews)
"Decent stay for a few nights"

Reviewed on Jul. 3, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Jul 10 to Jul 11
CA $230
CA $270 total
Jul 10 - Jul 11
includes taxes & fees
8.8/10 Excellent! (2,390 reviews)
"Really liked the area! Had a nice restaurant attached. Beds were very comfy"

Reviewed on Jul. 6, 2025

Hilton Chicago/Magnificent Mile Suites
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.

Discover the most popular places to visit in Chicago

What to do in Chicago

Frequently asked questions

How much does a Chicago vacation package cost?
You'll find cheap prices from CA $746 on Expedia for your Chicago getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Chicago costs.
What are the cheapest months to go to Chicago?
December, January and February are the best times to look for cheap Chicago vacation packages. Opting to travel in quieter periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Chicago?
Allow around 2 days for your Chicago vacation if you're hoping to immerse yourself in everything that makes this destination special. Wander around key neighbourhoods, including Central Chicago and Near North Side. Then check out major sights such as McCormick Place and Soldier Field. With a well-organized itinerary, you'll be kept busy with room for some relaxation too. Want to travel outside of Chicago? Consider an excursion or two.
Is it worth booking a vacation package to Chicago?
Chicago has everything you need for an amazing getaway --- views, dining and culture are just the start. Whether you want to visit sights like Navy Pier and Soldier Field, or take the path less travelled, there's plenty to explore on your Chicago vacation.
How to find the best Chicago package deals?
Use Expedia's filters to find some fabulous Chicago package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Chicago package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chicago vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking hotels and flights individually. Better still, you can tailor your Chicago trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Chicago?
If you're considering a spur-of-the-moment Chicago trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chicago?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Chicago.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Chicago.
  3. Decide how long to go away for: Now that you're more familiar with Chicago, you can work out the ideal length of your break. Pull together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Chicago vacation package.

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