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
Downtown Chicago showing a city

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 Michigan Avenue and Navy Pier 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

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is SAR 561 per night from May 1 to May 2
SAR 561
SAR 658 total
includes taxes & fees
1 May - 2 May
8.2/10 Very Good! (3,923 reviews)
"The staff was very helpful"

Reviewed on 22 April 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is SAR 675 per night from May 11 to May 12
SAR 675
SAR 903 total
includes taxes & fees
11 May - 12 May
8.8/10 Excellent! (2,079 reviews)
"My wife & I spent a 4 day weekend at the Swissotel & it was the best customer service we’ve ever experienced. The staff, specifically Kia, Joseph, and Bailey were more than accommodating & friendly. The hotel is right on the riverfront & extremely close to restaurants & shops. We can’t wait to go ..."

Reviewed on 22 April 2025

Swissotel - Chicago
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 SAR 685 per night from May 4 to May 5
SAR 685
SAR 804 total
includes taxes & fees
4 May - 5 May
8.8/10 Excellent! (2,141 reviews)
"The only thing was the pool was closed. But other then that we had a good stay"

Reviewed on 18 April 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,932 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.

Frequently asked questions

How much does a Chicago vacation package cost?
You’ll find cheap prices on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel 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’ll typically find lower prices on accommodations and flights.
How to find the best Chicago package deals?
Use Expedia’s filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it’s typically best to lock in your vacation package well in advance.
Is it cheaper to book a Chicago vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You’ll usually score a better deal than booking each component separately. And you’ll still have the freedom to create a customized Chicago vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Chicago?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.
How to plan a trip to Chicago?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that’s an affordable stay or a swankier getaway.
  3. Work out your trip length: Consider how long you’d like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you’re interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that’s left is to choose a Chicago vacation package that brings all your bookings together.

Discover the most popular places to visit in Chicago

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(1,805 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy 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