Cicero Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Your Cicero Vacation

The stress-free way to experience this city is with a customized Cicero vacation package. Base yourself in the neighborhood of Magnificent Mile, which is great for cafes, shopping and history or choose someplace else — our packages are all about you. Every trip to Cicero needs a well-thought-out itinerary. Fill yours with attractions like University of Illinois Chicago, United Center and Brookfield Zoo. Don't put off visiting this city any longer. The perfect Cicero vacation is a few quick clicks away with Expedia.

Top Cicero Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing amenities. friendly staff and clean rooms. Views from the balcony were so nice!

Reviewed on Jul. 12, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Ready to book your vacation to Cicero?

 

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Cicero 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 $202 per night from Aug 5 to Aug 6
CA $202
CA $238 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,957 reviews)
"Good stay"

Reviewed on Jul. 13, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $273 per night from Aug 10 to Aug 11
CA $273
CA $364 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,031 reviews)
"Great location ! Small but nice room ."

Reviewed on Jul. 13, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Aug 10 to Aug 11
CA $206
CA $242 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul. 11, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,819 properties in Cicero
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

Discover the most popular places to visit in Cicero

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
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
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

What to do in Cicero

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $61
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Cicero

Frequently asked questions

How much does a Cicero vacation package cost?
You'll find cheap prices from CA $688 on Expedia for your Cicero escape. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Cicero costs.
What are the cheapest months to go to Cicero?
If you're looking to book a cheap Cicero vacation package, consider travelling in January, February and November. You'll typically find better rates on flights and hotels during these quieter months --- perfect for a budget-friendly break.
How many days is enough for Cicero?
Allow around 2 days for your Cicero vacation if you're hoping to enjoy everything that makes this destination special. Stroll around popular neighbourhoods, including Near West Side and West Loop. Then make a beeline for top sights such as Brookfield Zoo and Credit Union 1 Arena. With a well-organized itinerary, you can keep busy with room for some downtime too. Want to venture beyond Cicero? Consider fitting in an excursion or two.
How to find the best Cicero package deals?
Use Expedia's filters to find some tempting Cicero package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Cicero package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Cicero vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations separately. Better still, you can tailor your Cicero escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Cicero?
If you've got your Cicero travel dates finalized, book early to snap up some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Cicero?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Cicero.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to factor in other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could arise during your trip to Cicero.
  3. Decide how long to go for: Now that you know more about Cicero, you can work out the right length of your vacation. Put together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Cicero 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.