Chicago Vacation Packages

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Top Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,610 reviews)
I loved the art, the bar, the area around the hotel, the fact its right next to the theatre, and how friendly everyone was!

Reviewed on Apr. 13, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 Apr. 13, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 Apr. 13, 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Good place if you need to be loop adjacent!

Reviewed on Apr. 7, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 Apr. 6, 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

Ready to book your vacation to Chicago?

 

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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 CA $188 per night from Apr. 20 to Apr. 21
CA $188
CA $220 total
includes taxes & fees
Apr 20 - Apr 21
8.2/10 Very Good! (3,872 reviews)
"Excellent quick friendly service! Staff is outstanding:)"

Reviewed on Apr. 11, 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 CA $216 per night from Apr. 16 to Apr. 17
CA $216
CA $295 total
includes taxes & fees
Apr 16 - Apr 17
8.8/10 Excellent! (2,038 reviews)
EXELLENT LOCATION
"Excellent location. We had a view of the lake and the river. Amazing stay. Resturant was five star and the bar downstairs cozy by fireplace. We parked in the garage upon arrival and walked every where. Will stay here again if ever back in Chicago."

Reviewed on Apr. 12, 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 CA $128 per night from Apr. 20 to Apr. 21
CA $128
CA $150 total
includes taxes & fees
Apr 20 - Apr 21
8.6/10 Excellent! (1,009 reviews)
"Excellent property. Safe location. Convenient check in and check out."

Reviewed on Apr. 10, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,933 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chicago vacation package cost?
You’ll find cheap prices from CA $683 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.

Discover the most popular places to visit in Chicago

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 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
Six Flags Great America featuring rides

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Chicago

Flyover in Chicago

Flyover in Chicago

CA $55
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $70
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $49
per adult
100% of travellers recommend
Color Factory Chicago Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.