East Side Holidays

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

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    Packages with flights are ATOL protected

Your East Side Holiday

Book a customized East Side holiday package and enjoy the delights of this neighbourhood from morning till evening. From its nature and walking to its unique personality and vibe, there's an endless list of reasons to visit East Side. Some top nearby attractions to visit during your trip to East Side include Calumet Park, Calumet Beach and Bronzeville Childrens Museum. Stop dreaming and start doing. When you're ready to book your next holiday to East Side, Expedia will help get you there.

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 17 - Jul 27

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    10 nights
    4.0 star property
    8.2/10 - Very good (2,730 reviews)
    "Staff was wonderful. Would’ve stayed an extra night if we didn’t need to go back to work."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £2,249
    £1,584
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Indoor wedding
    Jul 17 - Jul 27

    Swissotel - Chicago + Flight

    Downtown Chicago
    10 nights
    4.5 star property
    9.0/10 - Wonderful (3,349 reviews)
    "It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice."
    Reviewed May 26, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    Save 100% on your flight
    £2,673
    £1,679
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Smart TV
    Jul 17 - Jul 27

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    10 nights
    4.0 star property
    9.2/10 - Wonderful (489 reviews)
    "Amazing place"
    Reviewed May 26, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    Save 100% on your flight
    £2,924
    £1,890
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jul 17 - Jul 27

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    10 nights
    4.0 star property
    9.4/10 - Exceptional (2,516 reviews)
    "Clean and have a beautiful view of the lake"
    Reviewed May 26, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    Save 100% on your flight
    £2,871
    £1,959
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 17 - Jul 27

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    10 nights
    4.5 star property
    9.4/10 - Exceptional (3,714 reviews)
    "I enjoyed our stay at LondonHouse Chicago, Curio Collection by Hilton. Staff members were friendly and helpful! Housekeeping staff were friendly and on point with cleaning! My next visit to Chicago, I plan on staying there."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    Save 100% on your flight
    £2,838
    £1,941
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton

Where to stay in East Side

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

Downtown Chicago

5 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

Top hotels in East Side

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is £180 per night from 3 Jun to 4 Jun
£180
3 Jun - 4 Jun
includes taxes & fees
8/10 Very Good! (10,146 reviews)
"Very good location right in the heart of Downtown Chicago."

Reviewed on 26 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is £232 per night from 16 Jun to 17 Jun
£232
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,265 reviews)
"Staff was super friendly. Rooftop bar is awesome. The breakfast was fantastic. This may sound weird, but the toilet seats had abnormally large openings."

Reviewed on 27 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is £167 per night from 23 Jun to 24 Jun
£167
23 Jun - 24 Jun
includes taxes & fees
7.8/10 Good! (1,478 reviews)
"The hotel is in a very good condition, looks pretty nice and clean. The room was algo clean and it looks just like in pictures. Loved the location and that is very centric. Staff was nice as well"

Reviewed on 27 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,220 properties in East Side
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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an East Side travel package cost?
Browse and book everything in one place with our East Side travel packages, which start from only . Choose the flights and hotels that suit your travel plans. Then, add on one or two sightseeing tours to round off your unique escape.
If I'm not able to travel, can I cancel my East Side travel package?
If your holiday plans in East Side have changed, it's good to know that you can cancel or amend your booking. If you made your booking within the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose fees. For more information, check our Customer Service Portal.
How do I get a cheap travel package to East Side?
Find flights that fit in with your schedule, add a hotel room to your booking and watch the savings rack up with an East Side travel package. It's as simple as that! From flights and hotels to activities and rental cars, Expedia makes travelling cheap and easy. And with over 550 airlines and 1,000,000 hotel options globally to choose from, you'll never be short of choice.
Does Expedia offer Book Now, Pay Later East Side holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a dream getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday in multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in East Side?
Make sightseeing easy by staying in a hotel just a stone's throw away from East Side's main attractions. Millennium Park and Wrigley Field are two visitor favourites.
What are the top hotels in East Side?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are among the most popular properties in East Side. Why not take a look at the amenities and facilities at each and then decide?
How far in advance should I book my East Side holiday?
Your safest bet is to book early. Air carriers usually release flights nearly 12 months ahead of departure, and this is a perfect opportunity to pick up some of the cheapest prices. Boss just told you to take all your holiday days next week? Don't fret. 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 East Side travel package include?
Much of that depends on you. You can select from a range of East Side packages, such as a rental car, hotel and flight. You can also book a flight and a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your ideal East Side trip looks like, you're sure to save!
What should I know before booking an East Side travel package?
You'll land great savings when you combine your hotels, flights and rental cars into a travel package. Not only that, booking everything in one spot makes trip planning much easier. So why waste time or money? Whether you're putting together a fancy romantic getaway or an affordable family break, have a look at our package deals today.
Can I choose my airline with an East Side Expedia travel package?
Most definitely. We have access to over 550 partner airlines around the world, so you can customize your East Side getaway according to your travel needs.

Popular places to visit

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.