Lakeview Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Lakeview

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,080, price is now CA $773 per person
CA $773
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,702, price is now CA $843 per person
CA $843
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Thank you so much for a wonderful experience.

Reviewed on Oct 27, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was CA $1,341, price is now CA $834 per person
CA $834
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
The staff is very friendly and professional.

Reviewed on Oct 27, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,554, price is now CA $1,036 per person
CA $1,036
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Great location, amenities and wonderful staff.

Reviewed on Oct 27, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,749, price is now CA $1,169 per person
CA $1,169
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)

Where to stay in Lakeview

Find the best Lakeview areas and neighborhoods for the activities you enjoy most. Learn more about Lakeview
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Lakeview 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 $145 per night from Nov 22 to Nov 23
CA $145
CA $172 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very good! (10,130 reviews)
"Beautiful lobby, great location, outdated room, bathroom should’ve been gutted and redone long ago. Mold in the shower caulk, and the bathroom door wouldn’t close properly because it had swelled from long exposure to moisture. Two inch gap at the bottom of the door let in light from the hallway. ..."

Reviewed on Oct 27, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Nov 2 to Nov 3
CA $188
CA $223 total
Nov 2 - Nov 3
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
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 $163 per night from Nov 22 to Nov 23
CA $163
CA $194 total
Nov 22 - Nov 23
includes taxes & fees
River Hotel
See all 4,728 properties in Lakeview
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 Lakeview vacation package cost?
We make it easy for everyone to travel, with Lakeview vacation packages starting from just CA $773. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a few activities and tours to your travel itinerary?
How do I get a cheap travel package to Lakeview?
Search for flights that suit your schedule, add a hotel to your booking and watch how much you save with a Lakeview vacation package. It's that easy! From flights and hotels to tours and rental cars, Expedia is where your cheap getaway begins. And with more than 550 partner airlines and 1,000,000 hotels across the globe to pick from, you won't be short of choice.
Where should I stay in Lakeview?
Vacationers come from far and wide to see Wrigley Field and Lincoln Park Zoo in Lakeview. Book a hotel within a stone's throw of these top attractions to make sightseeing easy.
What are the top hotels in Lakeview?
If this will be your first time in Lakeview, make a reservation at Chicago Guest House Wrigleyville or The Chicago Hotel Collection - Wrigleyville. Both hotels offer friendly service and are top options with lots of travelers.
How far in advance should I book my Lakeview vacation?
Savvy travelers will likely want to book early. You can generally browse through international airfares on Expedia up to a year before your intended flight. If you're purchasing your ticket at the last minute, don't stress. Discounted prices sometimes occur in the last weeks before departure dates.
What does an Expedia Lakeview travel package include?
With Expedia, you can select any combination of flights, car rentals and hotels to create your ideal Lakeview package. Once you've made your booking, you can add on fun stuff like activities and tours. Don't forget — the more you bundle, the greater the savings!
What should I know before booking a Lakeview travel package?
Design deals that fit your budget with an Expedia package. Hotels, airfares, rental cars — we've got all of them. You'll save a tidy sum just for combining your bookings. Whether you're embarking on a skiing adventure or venturing someplace warm, your ideal getaway is only a few clicks away.
Can I choose my airline with a Lakeview Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our vacation packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Lakeview vacation package?
We get it — sometimes life doesn't go according to plan. If you've booked a Lakeview vacation package and need to cancel or amend it, we're here to help. It's always worth taking a look at our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it's more than 24 hours, your hotel, airline or car rental company may charge a fee.

Stay near popular Lakeview attractions

Wrigley Field

9.0/10 (11,704 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $57
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Chicago

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.