Deals on vacations and trips to Lakeside

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Lakeside flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $756, price is now $551 per person
$551
per person
Jan 15 - Jan 18
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,313, price is now $880 per person
$880
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,167, price is now $842 per person
$842
per person
Jan 11 - Jan 17
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
Price was $1,654, price is now $1,207 per person
$1,207
per person
Jan 18 - Jan 25
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This smoke-free resort features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,098, price is now $803 per person
$803
per person
Jan 15 - Jan 18
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Stay near popular Lakeside attractions

Burnison Galleries

You can spend time studying the exhibits at Burnison Galleries in Lakeside. Stroll along the beautiful beaches or visit the casinos in this romantic area.
See properties

Frequently asked questions

How much are vacation packages to Lakeside?
Packages, including flights and hotels in Lakeside, start from as little as $551. Turn your daydreams into reality and secure your dream vacation with Travelocity today.
How long should my Lakeside vacation be?
Around 2 nights is the average amount of time visitors spend in Lakeside. But the perfect trip length depends on how many treasured memories you want to make. Why not stay a couple of extra days and explore some off-the-beaten-path gems?
Where can I get the best vacation package deals for Lakeside?
No matter how you like to travel, Travelocity can help you score an unbeatable Lakeside package deal. All you need to do is select a combination from our 400 partner airlines and 1,000,000 worldwide properties.
Why should I purchase my Lakeside vacation package via Travelocity?
From amazing destinations to fun experiences, we have everything you need to satisfy your travel desires. Our 24/7 customer support will also make sure you're being taken care of before, during and after your trip. And don't stress if you notice a better price on your booking, we'll match it. That's our Price Match Guarantee.
Can I save money on my Lakeside car rental if I bundle it with a hotel or flight?
Sure can — combine your hotel, flight and car into a Lakeside vacation package and you can save plenty. With so much to uncover in Lakeside, having your own set of wheels will make exploring a joy. Once you've buckled yourself in, put the stereo on and make your way to Wrigley Field, a renowned attraction roughly 50 mi from Lakeside.
Which airport is best for Lakeside?
Lakeside has a couple of major airports to jet into — Midway Intl. Airport (MDW) (55 mi away from the city center) and South Bend Intl. Airport (SBN) (20 mi away from central Lakeside).
What is there to do in Lakeside?
Burnison Galleries is one of the awesome sights that make Lakeside such a tourist hot spot. But leave some extra time to explore the city's lesser-known attractions too. This is often where the best vacation memories are made.
Where should I stay when visiting Lakeside?
If you're searching for somewhere to lay your head, take a look at the Lakeside Cottage Short Walk To Association Beach!. It's the top choice for many travelers.

Photos of local treasures

Browse Lakeside vacation photos for more inspiration

A calm river with a bridge, surrounded by autumn-colored trees and a dock with boats.
A sunset over a body of water with two tents on a grassy field.
A pebble beach with a forested shoreline and calm sea.
A beach with seagulls flying over the water and a pier in the distance.
A lakeside scene with Adirondack chairs and a dock extending into the water.