Chicago Vacations from ₩823,275

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    Save up to ₩1,660,000 when you book a flight and hotel together*

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The Latest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was ₩1,057,825, price is now ₩823,275 per person
₩823,275
per person
Sep 5 - Sep 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,273 reviews)
The staff was so friendly and inviting! They offered me good recommendations for food and places to go! The room was clean and inviting with a gorgeous view of the park and near by buildings. As a solo traveler, I was happy to be close to points of interest like Millenium ParkNext time I am in Chicago, I would love to stay here again!

Reviewed on Aug 5, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩1,271,889, price is now ₩927,036 per person
₩927,036
per person
Sep 5 - Sep 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,879 reviews)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩1,373,061, price is now ₩1,032,017 per person
₩1,032,017
per person
Sep 5 - Sep 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,752 reviews)
Convenient location. Second stay

Reviewed on Aug 5, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was ₩1,119,240, price is now ₩904,552 per person
₩904,552
per person
Sep 5 - Sep 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (144 reviews)

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was ₩1,306,430, price is now ₩1,056,781 per person
₩1,056,781
per person
Sep 5 - Sep 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,160 reviews)
The bed was great and location was perfect. We enjoyed it.

Reviewed on Aug 3, 2026

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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 ₩225,067 per night from Aug 30 to Aug 31
₩225,067
₩267,581 total
Aug 30 - Aug 31
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 ₩229,394 per night from Aug 23 to Aug 24
₩229,394
₩272,725 total
Aug 23 - Aug 24
includes taxes & fees
8/10 Very Good! (1,919 reviews)
"Room was clean. Great walkable area with bars and restaurants nearby. Only a couple of blocks from the red line."

Reviewed on Aug 5, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩356,082 per night from Aug 7 to Aug 8
₩356,082
₩418,017 total
Aug 7 - Aug 8
includes taxes & fees
8.4/10 Very Good! (2,371 reviews)
"."

Reviewed on Aug 5, 2026

Hilton Chicago O'Hare Airport
See all 3,595 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 © 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."
See properties

Frequently asked questions

How much does a Chicago vacation package cost?
You'll find cheap prices from ₩823,275 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 many days is enough for Chicago?
To fully enjoy a Chicago vacation, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighborhoods like Central Chicago and Near North Side. If you've got some spare time, include a day trip or tour in your Chicago vacation itinerary.
Is it worth booking a vacation package to Chicago?
Chicago has everything you need for a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field, or take the road less traveled, you'll find plenty to do on your Chicago vacation.
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.

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