Lakeside Vacation Packages 2026 from $535

Lakeside flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$535

per person

Sep 10 - Sep 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.

Four Seasons Hotel Chicago

Downtown Chicago

$2,726

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$625

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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

Downtown Chicago

Save 100% on your flight

$547

per person

Oct 22 - Oct 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$932

per person

Sep 16 - Sep 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

Top Lakeside hotels deals

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside MI

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This cottage features a garden, laundry facilities, and barbecue grills.

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Lakeside MI

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This cottage features an outdoor pool and a hot tub. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also provided.

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Lakeside MI

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This vacation home includes a garden and barbecue grills.

Four Winds Casino Resort – New Buffalo

11111 Wilson Road New Buffalo MI

Free Cancellation

$109 nightly

$115 total

Sep 1 - Sep 2

Total with taxes and fees

A casino, 4 restaurants, and a 24-hour gym are all featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and free valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and an area shuttle.

Blue Chip Casino Hotel and Spa

777 Blue Chip Drive Michigan City IN

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$140 total

Aug 9 - Aug 10

Total with taxes and fees

This hotel features a casino, a full-service spa, and 3 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. There's a bar/lounge on site, and a coffee shop and wedding services are also provided.

Microtel Inn & Suites by Wyndham Michigan City

9834 W 400 N Michigan City IN

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$89 total

Aug 9 - Aug 10

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

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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.

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.

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Frequently asked questions

How much are vacation packages to Lakeside?

Packages, including flights and hotels in Lakeside, start from as little as $535. 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.