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Downtown Chicago Vacation Packages

Choose two or more items and save on your trip:

Top Holiday Package Deals in Downtown Chicago

Residence Inn Chicago Downtown/Loop
The Peninsula Chicago
The Godfrey Hotel Chicago
Hotel Essex Chicago
Royal Sonesta Chicago Riverfront

Where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago

Top Hotels in Downtown Chicago

Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3 out of 5
243 E. Ontario, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is CA $127 per night from Apr 18 to Apr 19
4.4/5Excellent! (1,378 reviews)

"Ok"…"

Reviewed on Apr. 12, 2021

Aloft Chicago Mag Mile
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5
85 East Wacker Drive, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is CA $212 per night from Apr 25 to Apr 26
4.6/5Wonderful! (2,694 reviews)

"The People at the main entrance are great....."…"

Reviewed on Apr. 9, 2021

LondonHouse Chicago, Curio Collection by Hilton
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is CA $187 per night from May 2 to May 3
4.3/5Excellent! (1,865 reviews)

"My room had an awesome view! No maid or cleaning service and they acted like it was a huge inconvenience to give me clean towels and more toiletries. Food was over priced abs chicken was burnt."…"

Reviewed on Apr. 12, 2021

Swissotel - 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.

Top things to do in Downtown Chicago

Frequently asked questions

How much does a Downtown Chicago vacation package cost?
Say yes to new adventures with our Downtown Chicago vacation packages, which start from only CA $968. Pick the hotels and flights that match your travel style. Then, add on a couple of sightseeing activities for an incredible escape.
If I'm not able to travel, can I cancel my Downtown Chicago vacation package?
If you’ve chosen a Downtown Chicago vacation package, you can amend or cancel it, but there may be a charge in some situations. You may be able to cancel and rebook at no cost if you’ve taken out your package within 24 hours. If it’s been longer than that, you may incur additional charges from your hotel, airline or car rental company. If you suddenly need to change your plans, make our Customer Service Portal your first stop for more info.
How do I get a cheap travel package to Downtown Chicago?
Our Downtown Chicago vacation packages offer plenty of savings for the savvy wanderer. How does as much as C$590 sound? That’s what you could save if you bundle your flights, hotels and extras (including tours) into a handy package. But cheap prices are just the beginning of your next amazing adventure. Book with Expedia and you’ll have more than 400 air carriers and 321,000 hotels around the world to choose from. Whatever your budget or style, there’s a vacation package to suit you.
Where should I stay in Downtown Chicago?
Urban explorers come from all corners of the globe to see John Hancock Center and Navy Pier in Downtown Chicago. Book a room close to these top attractions and visit them at your leisure.
What are the top hotels in Downtown Chicago?
If it’s your first visit to Downtown Chicago, book a room at Hyatt Regency Chicago or Congress Plaza Hotel. Both hotels offer comfy beds and are favorites with lots of travelers.
When is the best time of year to visit Downtown Chicago?
There’s no good time or bad time to take a break in Downtown Chicago. But if you’d like to score a good deal on your escape, consider the month of January. Hotel prices tend to be at their most expensive in October. Downtown Chicago can get very busy in June, July, August, so if you want to avoid the crowds, pack your bags for February, December, November.
How far in advance should I book my Downtown Chicago vacation?
The earlier, the better. Airlines usually advertise flights around a year ahead of departure, and this is your chance to land some of the cheapest prices. Just been told you need to take all your vacation days next week? No problem! Expedia are never short of fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Downtown Chicago travel package include?
Expedia has all you need to lock in Downtown Chicago escape, but what goes into your package is your choice. Select from a combination of rental cars, flights and hotels. Looking for a few activities to fill in your time? Once you’ve made your booking, you can add them on too. No matter your style or budget, there’s a package deal to match your needs.
What should I know before booking a Downtown Chicago travel package?
Design deals to suit your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your break. You’ll save precious cash just for bundling your bookings. Whether you’re heading away on a skiing adventure or sipping cocktails on a beach, your perfect vacation is just a few clicks away.
Does Expedia offer Book Now, Pay Later Downtown Chicago vacation packages?
Your bank balance shouldn’t prevent you from getting the best out of your vacation, so Expedia has devised a solution to help. Thanks to our partnership with online lender Affirm, it’s easy to book an unforgettable getaway that won’t drain your wallet. Just Book Now, Pay Later and take the financial stress out of budgeting for your journey.
Can I choose my airline with a Downtown Chicago Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to select from globally. With such a huge range of choice, finding the ideal carrier to whisk you off to Downtown Chicago will be a breeze.