Chicago Vacations

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Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Find the Best Chicago Vacation Packages

Chicago Hotel Deals

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 AEDĀ 426 per night from Nov 22 to Nov 23
AEDĀ 426
AEDĀ 507 total
22 Nov - 23 Nov
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 426 per night from Nov 11 to Nov 12
AEDĀ 426
AEDĀ 506 total
11 Nov - 12 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 389 per night from Dec 10 to Dec 11
AEDĀ 389
AEDĀ 463 total
10 Dec - 11 Dec
includes taxes & fees
River Hotel
See all 5,371 properties in Chicago
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.

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by Ā© City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."
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Frequently asked questions

How much does a Chicago vacation package cost?
You'll find cheap prices 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 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, favorite 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.

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