Chicago Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
per person
Mar. 13 - Mar. 16
found 12 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
The whole lobby was under construction… made for a loud and dusty experience. Staff seemed a bit pushy … didn’t feel warmly welcomed.

Reviewed on Nov. 24, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Feb. 14 - Feb. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,241 reviews)
Upgraded to a suite upon checkin! Incredible room!!

Reviewed on Dec. 20, 2024

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Feb. 20 - Feb. 23
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,142 reviews)
Beautiful new hotel in the heart of Chicago!

Reviewed on Dec. 21, 2024

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Mar. 5 - Mar. 9
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.8/10 Excellent! (383 reviews)
Property is amazing and the rooms are very nice! It is an amazing stay, but just a couple hiccups. One is the parking which is really strange, you have to block the sidewalk and walk in to have them open the garage, kind of strange, they should add just a card reader to the garage door, or a camera for the front desk to permit drivers to enter. The gold perk we received a 10-15$ bottle of wine ( I’m not hating I love wine) but the last hotel with this perk hooked us up with a 200$ bottle. Still a very beautiful stay and very peaceful… the rooms are huge.

Reviewed on Dec. 21, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 5 - Mar. 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (275 reviews)
I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location

Reviewed on Dec. 7, 2024

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 hotel + flight trips in Downtown Chicago

Ready to book your vacation to Chicago?

 

Choose your dates

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 $132 per night from Jan. 16 to Jan. 17
CA $132
CA $154 total
includes taxes & fees
Jan 16 - Jan 17, 2025
7.8/10 Good! (8,261 reviews)
"Beautiful hotel with a great location"

Reviewed on Dec. 19, 2024

Congress Plaza Hotel
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
The price is CA $159 per night from Jan. 8 to Jan. 9
CA $159
CA $186 total
includes taxes & fees
Jan 8 - Jan 9, 2025
8.2/10 Very Good! (3,225 reviews)
"Everything was great. Hotel, happy hour Everyday. Complimentary breakfast. Wow!"

Reviewed on Dec. 19, 2024

Embassy Suites by Hilton Chicago Downtown River North
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Jan. 10 to Jan. 11
CA $200
CA $277 total
includes taxes & fees
Jan 10 - Jan 11, 2025
9/10 Wonderful! (3,114 reviews)
"I loved my stay. One of the best hotels in the city."

Reviewed on Dec. 18, 2024

Hyatt Regency Chicago
See all 4,901 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 $507 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.
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
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
Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Chicago

Flyover in Chicago

Flyover in Chicago

CA $54
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $69
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

CA $63
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge 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.