Chicago Vacations from AED2,500

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The Latest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,269 reviews)
Beautiful space, right near the lake. Also has a cozy little restaurant on the 1st floor

Reviewed on 3 June 2025

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
No reviews
Perfect location. The roads are very clean and most importantly the mattress was very comfortable. We had the option to use a non pet friendly rooms since I have allergies and got a room higher floor for a free upgrade. So far one of the best hotels I’ve ever stayed at.

Reviewed on 24 May 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,598 reviews)
This is the second time that we have stayed at the Trump hotel. It’s a beautiful property in a prime location. There are amazing views of the river and lake. The hotel is within walking distance of shopping, restaurants, and other fun sites! The spa is provides great service! I will definitely stay there again!

Reviewed on 1 June 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,754 reviews)
Our stay was ok. The hotel was not as updated as the pictures on the site shows. The carpets were stained and worn down, and the sheets and rooms were very old and outdated. The rooftop looked nothing like the photos. Otherwise it’s in a great location.

Reviewed on 31 May 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.4/10 Very Good! (1,733 reviews)
Location was great, walkable to anywhere in downtown Chicago, Millennium Park, Soldier Field, etc.

Reviewed on 27 May 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

5 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

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 AED 526 per night from Jul 3 to Jul 4
AED 526
AED 617 total
includes taxes & fees
3 Jul - 4 Jul
7.8/10 Good! (8,826 reviews)
"The facility has a great location in walking distance to many attractions. The family suite had a small bathroom with limited space."

Reviewed on 3 June 2025

Congress Plaza Hotel
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 490 per night from Jul 1 to Jul 2
AED 490
AED 575 total
includes taxes & fees
1 Jul - 2 Jul
9.2/10 Wonderful! (3,134 reviews)
"Nice clean hotel. Close to it all downtown"

Reviewed on 2 June 2025

citizenM Chicago Downtown
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 525 per night from Jun 30 to Jul 1
AED 525
AED 727 total
includes taxes & fees
30 Jun - 1 Jul
8.8/10 Excellent! (1,009 reviews)
"Absolutely top tier!! Definitely a whole vibe."

Reviewed on 30 May 2025

The Westin Michigan Avenue Chicago
See all 5,256 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 AED2,500 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)

Wrigley Field is one of the more well-known attractions to visit during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its fascinating museums.

Navy Pier
Six Flags Great America featuring rides

Six Flags Great America

4.5/5(347 reviews)

Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.

Six Flags Great America