Tips for Finding A Bargain at Randolph St Market & Beyond

As a 16-year veteran of vintage shopping (I started young), I’m constantly on the hunt not only for a treasure at garage sales, thrift stores or flea markets, but for a good deal. It’s easy to have a stylish home or wardrobe with an unlimited budget– the challenge and the joy lies in finding a pristine 1940s dress for $1 in a dusty attic or beating someone to a Midcentury Modern lamp for $5 at a rummage sale.
Curated vintage markets, however, can be intimidating. Dealers know what they have and price accordingly– is it still possible to find a bargain at this type of venue? Since I’m a collector and dealer I don’t have to worry about profit margins but do have to keep to a tight budget on my junking jaunts. At the season opener of the Randolph Street Market 2 weekends ago I set a challenge for myself: to spend $20 or less. Below are some tips on what I did and how to find a deal wherever you go.

1. Be Willing to Dig
When I’m shopping higher priced markets I seek out the ‘junk’ man or woman; they’re easily spotted by the lack of price tags on their merchandise, the precarious piles of goods on their tables and cartons containing a mishmash of items. One dealer at another Chicago-area flea market, Kane County, puts out cardboard boxes brimming with newspaper-wrapped objects that shoppers uncover in search of their collectibles. While it takes more time and work to go through these types of booths, the reward is a pile of vintage for very little money.
2. Consider Fixer Upper/Imperfect Pieces
If you’re a casual collector or wear vintage clothing every day (like I do), it’s important to consider items that are flawed or need some d.i.y. help. Of course we have all seen the fabulous “before & after” posts of furniture finds at Apartment Therapy and Design Sponge; paint or new knobs/hardware can completely change the character of a piece. I’m lucky enough to have a talented seamstress mom so I can pick up dresses that are missing buttons, have split seams or need to be re-hemmed. Think creatively; bike baskets, wood crates and even Pyrex baking dishes can be easily cleaned up and can serve as handy storage in cramped apartments. Dealers will price ‘as is’ items lower or if you notice damage use it as a jumping off point for haggling.
3. Haggle
Yes, this might seem obvious but prices are rarely ‘set’ at flea markets and garage/yard sales– just don’t be pushy or rude in the pursuit of a bargain. The easiest way to start haggling is to ask the seller: “Is this your best price?” or “Could you do better?”. Most sellers are going to be willing to work with customers, especially when purchasing more than one item. Don’t insult the seller by offering a $1 for a $20 item, aim for knocking down the price 20 to 30 percent. Another strategy is to buy a more expensive item (ie a piece of furniture) then ask if a smaller item can be thrown in free to sweeten the deal. Be sure to show real interest in an item and chat about what you envision doing with it– if I’m buying vintage ephemera or snapshots I bring up being an artist, with clothing or accessories I explain that my wardrobe is completely vintage and secondhand. Dealers are collectors too and want to see their pieces go to a good home!

4. Build a Relationship with Dealers
I make it a point to have conversations with dealers that I buy from or who have interesting booths. I’ll usually ask them how long they’ve been in the business, where they’re from and what they collect. Full-time sellers will often have a booth at the same shows every week or month, in the same spot. Once they get to know me they’ll be on the look out for items that fit my taste and also be more willing to give me a discount (see above tip). Inbetween flea market seasons dealers also have to unload goods that didn’t sell or are slightly damaged; their regular customers can get first dibs on these vintage clearouts. Dealers also specialize in certain areas of collecting and serve as indispensable sources of information that can be hard to find even on the Internet. Besides getting a deal, building a relationship with dealers can lead to friendships with fellow vintage-crazed individuals (I met my friend Albert at a flea market 2 years ago when I bought some vintage photo booth photos from him!).
5. Focus on Smaller Pieces
If my budget is tight but I want to wander the market for a while I focus on smaller items that take a while to sift through like vintage snapshots, postcards, novels and cookbooks. To update my decor I look for planters, drawings or small paintings and suitcases (that also serve as storage). Barware is often inexpensive, swizzle sticks are very 1960s Mad Men and can be picked up for as little as 25 cents. If dresses are priced too high I’ll instead look for a whimsical brooch or a lace collar to change the look of a frock already in my warddrobe. Souvenir scarfs, old menus and maps can be framed or pinned on a wall as a cheap form of art. Other tid bits I look for include keychains, buttons, political pins, wax seals, glass bottles (to use as vases), dice from Las Vegas casinos and celluloid Cracker Jack charms.
6. Go on the Second Day
While the selection is the best on the first day, the best prices will be on the last day of a flea market. If possible, target the out-of-town dealers who want to clear out as much merchandise as possible before heading back home. At some markets, dealers will replenish their stock on the second day while other sellers might only be there on the second day due to other obligations. Even in the last hour of a sale I have managed to scoop up piles of treasures for much less than the marked prices.


The photos thus far through this post (and the next 3) are from a booth at the Randolph Street Market that specialized in nautical goods. The husband and wife team are based out of Wisconsin and even in the first hour of the sale were open to bargaining. They had some of the most unusual items at the market and the prices were also reasonable.
Can’t you imagine one of those ship portholes mounted on a wall? The wooden floaters (?) were my favorite item of the booth– can’t remember how much they were, probably around $7, but they would look best as a cluster on a wall or as a sculptural element in an room.
Sadly this AMAZING hand and the heart handcarved folk sculpture was out of my budget (it was $45). Definitely a fair price as I’d never come across anything remotely like it before.
What did I end up coming home with for under $20? The two cardboard signs above came from the nautical booth and are from the 1930s or 1940s. They are meant for use in a diner but were deadstock that the dealers found in a warehouse. The text caught my eye as well as the suggestive nature of the phrasing (or is that just me?).


They were marked at $8 each but since I bought two they were only $6 each. I have plans to frame them and put them up in my kitchen.


You’re all aware of my passion for vintage jewelry– following my own advice I made for the ‘junk’ man and pawed through all his unpriced pieces. After 20 minutes of digging I asked him how much the badge above and the two pins below would be– he sold them to me for $5 total.

I apologize for the un-PC pin, I bought it because it was so quirky and definitely wouldn’t be something that a company would hand out today. It wasn’t until I photographed it that I realized the bit of fur was in the shape of a seal (!!). Poor seals. 🙁 Apparently this factory is still in existence, I’m curious what sort of souvenirs they’re handing out now?


The rooster pin is small and well loved but he’ll be happy on one of my blazers come autumn.
What are your tips for finding bargains? What smaller items do you keep an eye out for while junking?
[Be sure to visit other people’s vintage finds over at Apron Thrift Girl’s Thrift Share Monday!]


Comments 0

  1. The biggest thing I try to do when bargain hunting is avoiding the for-profit thrifts, like Value Village. They are just so much more expensive, and you have to pay tax on top of it too.

    My heart sort of sank when I read your example about a lamp. I had my hands on a Lotte Bostlund lamp for $5 but put it down. When I came to my senses it was gone!

  2. Great tips you old young junker you.What a great market as well I loved all the mermaids I saw and those portholes are great,I didnt even see the fur was a seal till you said so.That rooster is so cute too.

  3. These are great tips! I'm also an extreme bargainer, haha. As a result, most of my antiques and dresses came to me dirty and a bit broken… but a little tlc makes them functional again, plus I like the worn-out patina.
    That seal pin may be un-pc, but it's pretty funny! Wonderful finds!

  4. I went to that market one and only time when I was in Chicago visiting my sister.I ended up buying a vintage board game that was framed for my sons room.The dealer overheard me saying I didn't want to at first because I couldn't get it back on the plane. He then came over and offered to ship it for me for free! It was a great experience there. Lots of different types of items than our markets here have. I can't wait to go again some day.

  5. my #1 tip that my husband actually taught me is to point out the item's flaws to get the price down. as in "oh, look there's a stain/chip right here, can you take a few bucks off?" this all stems form a dining room table I bought by myself at the alameda flea. i though i got a great deal but once i got it home we noticed a tiny penis and balls etching on it(it's small but it's there)! i could have knocked off another $30 for that one at least 🙂

  6. These are such brilliant and well though through tips. I wish I could haggle! I find that so hard to do. Instead I put the thing I want back with a sigh and say something like, "I'm not sure. I just don't think I can justify spending that". Sometimes it results in an immediately reduced offer. Great photos too. In answer to your question, I'm currently reading non-fiction as well: Waterlog by the late Roger Deakin. It's an account of his wild water swimming all over Britain. Beautiful.

  7. Yes for tips! I love the thrill of the hunt for vintage goodies, especially at speciality markets. Dealers do know their prices, but that doesn't mean that they aren't willing to break you a deal! Every time I look at pictures from this market, I let out little screams of joy. Oh, how I wish I could have gone! Oh, and I think we will be in Chicago on either the 21st or 22nd of July…still trying to work it out! eek! So excited! xx

  8. I occasionally get to Grayslake and even more rarely get to Kane but I have nevr been to Randolph St. I'll have to put that on my list.
    The seal fur pin is actually made of seal fur. I have seal shaped toys from Alaska that missionaries from our church brought back in the early 60s.
    I think one company used to hand out Walrus tusk (or some sort of teeth) keychains.

  9. I love that you have included tips as well. A few weeks ago I started a Frugal Friday's linky on my blog. I would love it if you would take the time to link this post up…and think about returning each week with any frugal type posts you do!

  10. This is such a fabulous article Leilani, I absolutely LOVE IT!! You've given your readers such a wonderful shopping guide, and the items you picked to showcase are just right, ahhhhh, can't wait to see you and have your marvelous eye and energy on the scene XXOO

  11. Love all the the cool stuff in the pictures and great tips. I don't do many flea markets or rummage sales but I tend to find a lot of gems at estates in not-so-good areas of town. The things we do for bargains! Great blog 🙂

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