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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

Residence Inn Chicago Downtown/Loop

3.5 out of 5
Theatre District
CA $1,269

CA $968

per person
May 27 - Jun 3
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
4.7/5Exceptional! (968 reviews)

"The actually had hot food service rather than the idiotic "new normal" of sack lunches. They actually had daily room service rather than the "new normal" of... well... not cleaning rooms daily as I've encountered this past year.…"

Reviewed on Apr. 6, 2021

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Streeterville
Save 100% on your flightCA $3,223

CA $2,474

per person
May 27 - Jun 3
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
4.9/5Exceptional! (999 reviews)

"From the time we pulled up at the Peninsula Hotel in downtown Chicago. The staff go out of there way to make you feel comfortable.…"

Reviewed on Apr. 6, 2021

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
River North
CA $1,302

CA $1,061

per person
May 27 - Jun 3
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
4.3/5Excellent! (1,664 reviews)

"I like the I/O Roofscape, very classy…"

Reviewed on Apr. 11, 2021

Hotel Essex Chicago

Hotel Essex Chicago

4 out of 5
The Loop
CA $1,294

CA $1,073

per person
May 27 - Jun 3
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
4.3/5Excellent! (1,049 reviews)

"All though the room was excellent, there were parties going on to late in the night and the smell of cigarettes and pot was thick in the hallways and eventually migrated into our room. I have stayed here before without issue, but will be looking at other places in the future.…"

Reviewed on Apr. 5, 2021

Royal Sonesta Chicago Riverfront

Royal Sonesta Chicago Riverfront

4 out of 5
The Loop
CA $1,417

CA $1,186

per person
May 27 - Jun 3
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
4.2/5Very Good! (2,398 reviews)

"Great location. Close to the River Walk and walkable distance to the Art Institute. Lots of restaurants near by.…"

Reviewed on Apr. 11, 2021

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
    Magnificent Mile - River North

    Magnificent Mile

    Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

    Find hotel + flight trips in Magnificent Mile
    The Loop - Downtown featuring a river or creek

    The Loop

    4 out of top 10 points of interest in this area

    4.5/5Wonderful!(725 area reviews)

    Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

    Find hotel + flight trips in The Loop
    Chicago which includes modern architecture and a city

    Lincoln Park

    5/5Exceptional!(20 area reviews)

    Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

    Find hotel + flight trips in Lincoln Park
    Gold Coast featuring street scenes as well as a couple

    Gold Coast

    Enjoy upscale shopping, varied dining experiences and waterfront walks at this affluent suburb set on the shores of Lake Michigan.

    Find hotel + flight trips in Gold Coast
    South Loop which includes a high-rise building and a city

    South Loop

    1 out of top 10 points of interest in this area

    4/5Very Good!(31 area reviews)

    South of downtown Chicago, this neighborhood features cultural activities, sports and convention centers and a great dining and nightlife scene.

    Find hotel + flight trips in South Loop

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
See all 939 properties in Downtown 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

Image for 360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck (Hancock Center)

CA $38
Per adult
84% of travellers recommend
360 CHICAGO Observation Deck (Hancock Center)
Image for Chicago Mob Tour: Criminals & Gangsters Bus Tour

Chicago Mob Tour: Criminals & Gangsters Bus Tour

CA $57
Per adult
90% of travellers recommend
Chicago Mob Tour: Criminals & Gangsters Bus Tour
Image for Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS: Admission to Top 5 Chicago Attractions

CA $137
Per adult
94% of travellers recommend
Chicago CityPASS: Admission to Top 5 Chicago Attractions
See all activities in 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.

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