Chicago Vacations from AED1,830

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The Latest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
May 24 - May 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
9.2/10 Wonderful! (1,665 reviews)
The staff was amazing! Each one was very helpful and kind! The room was excellent, super clean, and comfortable! Will be staying here again!!

Reviewed on 13 April 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
May 24 - May 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Only thing was no communication on the pool location and the arcade games so I just didn't go and how to work the stove other that it was a beautiful experience. I think you should let people smoke on the balcony. I mean it is a expensive location and marijuana is legal a recreational use think about it.

Reviewed on 13 April 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
May 24 - May 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Rooms were clean and spacious. Disappointed at the bar staff, not very engaging.

Reviewed on 6 April 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
May 24 - May 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Beautiful hotel. Extremely clean. Conveniently located.

Reviewed on 12 April 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
May 24 - May 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
The coffee and tea area was fully stocked and there were many places to sit that were open and comfortable. The staff was very helpful and one of the restaurants (The Fillmore) associated with the property was excellent.

Reviewed on 13 April 2025

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 AED 496 per night from Apr 20 to Apr 21
AED 496
AED 583 total
includes taxes & fees
20 Apr - 21 Apr
8.2/10 Very Good! (3,880 reviews)
"Good clean room. Great breakfast service."

Reviewed on 13 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 AED 573 per night from Apr 16 to Apr 17
AED 573
AED 780 total
includes taxes & fees
16 Apr - 17 Apr
8.8/10 Excellent! (2,046 reviews)
"Nice place, staff was very friendly. I would definitely recommend staying!"

Reviewed on 13 April 2025

Swissotel - Chicago
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is AED 338 per night from Apr 20 to Apr 21
AED 338
AED 397 total
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (1,009 reviews)
"Excellent property. Safe location. Convenient check in and check out."

Reviewed on 10 April 2025

Crowne Plaza Chicago West Loop by IHG
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 from AED1,830 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
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
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