East Side Holidays from £974

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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.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was £1,291, price is now £974 per person
£974
per person
2 Oct - 7 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.4/10 Very good! (3,939 reviews)
This hotel is in a perfect location and a great price! It’s a boutique hotel and quite old but the room was clean with nice decor.

Reviewed on 14 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,766, price is now £1,225 per person
£1,225
per person
2 Oct - 7 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on 14 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,207, price is now £1,646 per person
£1,646
per person
2 Oct - 7 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good! All in all, a very happy experience.

Reviewed on 14 Jul 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,389, price is now £1,059 per person
£1,059
per person
2 Oct - 7 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
I wish the space was bigger. It was too tight for me and my young girls but the staff was so extra nice and welcoming.

Reviewed on 14 Jul 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,412, price is now £1,080 per person
£1,080
per person
2 Oct - 7 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The room was much smaller than expected and the ac unit was super loud but you get used to it eventually. Other than that, reallllly good hotel to stay at. Walking distance from everything!

Reviewed on 14 Jul 2026

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
A busy city street with tall buildings, a bus, and cars.

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

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 £146 per night from 27 Jul to 28 Jul
£146
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,744 reviews)
"Front desk person were very r"

Reviewed on 15 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £233 per night from 26 Jul to 27 Jul
£233
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,913 reviews)
"Staff was fantastic and always ready to help; from the front door to the room door!"

Reviewed on 15 Jul 2026

Omni Chicago Hotel
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 £168 per night from 10 Aug to 11 Aug
£168
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,264 reviews)
"No parking at hotel. Had to park 5 blocks away and carry bags."

Reviewed on 15 Jul 2026

Congress Plaza Hotel
See all 4,027 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 £974. 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.

Stay near popular East Side attractions

Calumet Park

8.0/10 (1 review)
Explore the great outdoors at Calumet Park, a lovely green space in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£31
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.