Chicago Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Apr. 17 - Apr. 19
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,340 reviews)
Would definitely be coming back to this hotel

Reviewed on Jan. 20, 2025

Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Apr. 17 - Apr. 20
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (17 reviews)
How nice it was and how close it was

Reviewed on Jan. 13, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Mar. 15 - Mar. 18
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (428 reviews)
Fabulous. Always enjoy my stay here. They are always super nice and accommodating. The building is spotless. Love having a washer and dryer in the room.

Reviewed on Jan. 12, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Mar. 15 - Mar. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (282 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on Jan. 20, 2025

Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
per person
Apr. 17 - Apr. 20
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (CHI)
8.4/10 Very Good! (999 reviews)
Willie checked us in.....what an amazing man and all the other staff at the dront desk!!!! Exceptional service...room and overall experience. Sister trip this go around. Will bring my husband back soon!!! Thank you all for a wonderful experience.

Reviewed on Jan. 20, 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 Millennium Park 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

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 CA $118 per night from Feb. 7 to Feb. 8
CA $118
CA $138 total
includes taxes & fees
Feb 7 - Feb 8
7.8/10 Good! (8,400 reviews)
"Very clean. Friendly staff. Security was always alert. Decent gym for a hotel too!"

Reviewed on Jan. 19, 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Feb. 3 to Feb. 4
CA $126
CA $148 total
includes taxes & fees
Feb 3 - Feb 4
8.6/10 Excellent! (3,719 reviews)
"I enjoyed my stay no complaints ☺️"

Reviewed on Jan. 20, 2025

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Feb. 19 to Feb. 20
CA $136
CA $159 total
includes taxes & fees
Feb 19 - Feb 20
8.6/10 Excellent! (2,802 reviews)
"Staycation was very nice. Spa is the absolute best! Service and Ambiance was perfect."

Reviewed on Jan. 19, 2025

Eurostars Magnificent Mile
See all 4,978 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 $776 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

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
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
McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Chicago

Flyover in Chicago

Flyover in Chicago

CA $55
per adult
96% 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
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.