Chicago Vacations from ₩903,104

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The Latest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩1,202,021, price is now ₩903,104 per person
₩903,104
per person
Sep 5 - Sep 7
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
8.2/10 Very Good! (2,854 reviews)
Front desk staff is very friendly and helpful. The room is a bit dated and small, layout is awkward. The TV doesn't work well. For a 4* hotel, I expect better quality toilet paper (it's the lowest grade). Sink doesn't drain quickly. I was stuck in Chicago due to flight cancellations so paid over $400 a night and it's surged pricing since all the airport hotels were out. Location is really convenient though.

Reviewed on Jul 22, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ₩1,410,644, price is now ₩980,322 per person
₩980,322
per person
Sep 5 - Sep 7
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)
One of the best places we’ve ever stayed. We had an amazing view of downtown Chicago from our floor, and our executive suite was clean and comfortable. We thoroughly enjoyed our stay and would definitely come back. The customer service and our room were excellent.

Reviewed on Jul 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ₩1,522,873, price is now ₩1,068,148 per person
₩1,068,148
per person
Sep 5 - Sep 7
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ₩1,685,350, price is now ₩1,249,784 per person
₩1,249,784
per person
Sep 5 - Sep 7
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ₩1,388,532, price is now ₩1,061,204 per person
₩1,061,204
per person
Sep 5 - Sep 7
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)

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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is ₩279,437 per night from Aug 6 to Aug 7
₩279,437
₩318,499 total
Aug 6 - Aug 7
includes taxes & fees
Hyatt Regency O'Hare Chicago
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 ₩271,896 per night from Aug 9 to Aug 10
₩271,896
₩323,289 total
Aug 9 - Aug 10
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩442,072 per night from Aug 9 to Aug 10
₩442,072
₩525,607 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,932 reviews)
"There wasn’t any Clean linen available upon request. Sheets / Towels etc. The Breakfast Menu/ Bar was great."

Reviewed on Jul 20, 2026

The Wade
See all 3,622 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 ₩903,104 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.